Home / Articles / Carbocations and Electrophilic Reactions

Carbocations and Electrophilic Reactions

George Andrew Olah 1
George Andrew Olah
1 Faculty of Chemistry, Case Western Reserve University, USA
10.1002/anie.197301731
Published 30 November 1974
Communication , Volume 44, Issue 5, 173-212
259
Share
Cite this
GOST
 | 
Cite this
GOST
Copy cite
Olah G. A. Carbocations and Electrophilic Reactions // Russian Chemical Reviews. 1975. Vol. 44. No. 5. pp. 173-212.
GOST all authors (up to 50)
Copy cite
Olah G. A. Carbocations and Electrophilic Reactions // Russian Chemical Reviews. 1975. Vol. 44. No. 5. pp. 173-212.
RIS
 | 
Cite this
RIS
Copy cite
TY - JOUR
DO - 10.1002/anie.197301731
UR - https://rcr.colab.ws/publications/10.1002/anie.197301731
TI - Carbocations and Electrophilic Reactions
T2 - Russian Chemical Reviews
AU - Olah, George Andrew
PY - 1975
DA - 1974/11/30
PB - ANO Editorial Board of the journal Uspekhi Khimii
SP - 173-212
IS - 5
VL - 44
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors)
Copy cite
@article{1975_Olah,
author = {George Andrew Olah},
title = {Carbocations and Electrophilic Reactions},
journal = {Russian Chemical Reviews},
year = {1975},
volume = {44},
publisher = {ANO Editorial Board of the journal Uspekhi Khimii},
month = {Nov},
url = {https://rcr.colab.ws/publications/10.1002/anie.197301731},
number = {5},
pages = {173--212},
doi = {10.1002/anie.197301731}
}
MLA
Cite this
MLA
Copy cite
Olah, George Andrew. “Carbocations and Electrophilic Reactions.” Russian Chemical Reviews, vol. 44, no. 5, Nov. 1975, pp. 173-212. https://rcr.colab.ws/publications/10.1002/anie.197301731.
Views / Visits
10 / 10

Abstract

The general concept of carbocations encompasses all cations of carbon containing compounds which can be differentiated into two distinct classes: trivalent ("classical") carbenium ions and pentacoordinated ("nonclassical") carbonium ions. In this paper the preparation and structural study (by NMR, IR, Raman and ESCA spectroscopy) of stable carbenium ions and carbonium ions are discussed. As is well known, trivalent carbenium ions play an important role in electrophilic reactions of π- and n-donor systems. Similarly, pentacoordinated carbonium ions are the key to electrophilic reactions of σ-donor systems (single bonds). The ability of single bonds to act as σ-donor lies in their ability to form carbonium ions via triangular two electron, three-center bond formation. Consequently there seems to be no principle difference between the electrophilic reactions of π- and σ-bonds except that the former react more easily, even with weak electrophiles, whereas the latter necessitate more severe conditions. The role of carbocations in electrophilic reactions of π- and σ-donor systems is discussed.

References

1.
Stable carbocations. CXXXVII. Cycloheptenyl, cyclooctenyl, and cyclononenyl cations
Olah G.A., Liang G.
Journal of the American Chemical Society , 1972
2.
e_1_2_1_2_2
Curie M.
C. R. hebd. Séances Acad. Sci. , 1910
3.
e_1_2_1_2_3
Bethell D.
1967
4.
Stable, Long-lived Carbonium Ions
OLAH G.A.
Chemical & Engineering News , 1967
6.
e_1_2_1_4_2
Huisgen R.
Angew. Chem. , 1955
7.
e_1_2_1_5_2
Hedström B. O.
Ark. Kemi , 1952
8.
e_1_2_1_5_3
Bonnet R.
J. chem. Soc. (London)
9.
Does Carbon Utilize 3dOrbitals in Bonding?
Jaffé H.H.
Journal of Chemical Physics , 1953
10.
The Use of 3dOrbitals in Bonding by Carbon
Gillespie R.J.
Journal of Chemical Physics , 1953
11.
Pentaco-ordination
Muetterties E.L., Schunn R.A.
Quarterly Reviews Chemical Society , 1966
12.
e_1_2_1_7_2
Vogel E.
Angew. Chem. , 1964
13.
e_1_2_1_8_2
Grignard V.
Compt. rend. , 1914
14.
Neighboring Carbon and Hydrogen. XI. Solvolysis of exo-Norbornyl p-Bromobenzenesulfonate1,2,3
Winstein S., Trifan D.
Journal of the American Chemical Society , 1952
15.
e_1_2_1_9_2
Glasstone S.
1941
16.
Bridged, non-classical carbonium ions
Sargent G.D.
Quarterly Reviews Chemical Society , 1966
17.
Centenary Lecture. Nonclassical ions and homoaromaticity
Winstein S.
Quarterly Reviews Chemical Society , 1969
18.
The Nonclassical Ion Problem
BROWN H.C.
Chemical & Engineering News , 1967
19.
Stable carbonium ions. C. Structure of the norbornyl cation
Olah G.A., White A.M., DeMember J.R., Commeyras A., Lui C.Y.
Journal of the American Chemical Society , 1970
20.
e_1_2_1_11_2
J. chem. Soc. [London]
22.
Über die Gleichgewichts-Isomerie zwischen Bornylchlorid, Isobornylchlorid und Camphen-chlorhydrat
Meerwein H., van Emster K.
Berichte der deutschen chemischen Gesellschaft (A and B Series) , 1922
23.
e_1_2_1_14_2
Armitt J. W.
J. chem. Soc. [London]
24.
THE COMMON BASIS OF INTRAMOLECULAR REARRANGEMENTS1
Whitmore F.C.
Journal of the American Chemical Society , 1932
25.
e_1_2_1_15_3
Chem. Zbl.
27.
INTERACTION OF FRIEDEL-CRAFTS CATALYSTS WITH ALKYL HALIDES AND AROMATIC HYDROCARBONS
Brown H.C., Pearsall H., Eddy L.P.
Journal of the American Chemical Society , 1950
29.
e_1_2_1_19_2
Marckwald W.
Ber. dtsch. chem. Ges. , 1903
30.
e_1_2_1_20_2
Clar E.
Chem. Ber. , 1949
31.
e_1_2_1_21_2
Harley‐Mason J.
Chem. and Ind.
32.
Unstable intermediates
Rosenbaum J., Symons M.C.
Molecular Physics , 1960
33.
e_1_2_1_21_4
Rosenbaum J.
J. Chem. Soc.
34.
e_1_2_1_22_2
Clar E.
J. chem. Soc. [London]
35.
Carbonium Ions
Deno N.C.
Progress in Physical Organic Chemistry , 1964
36.
For preliminary communications and lectures see:G. A.Olah Conference Lecture at the 9th Reaction Mechanism Conference Brookhaven New York August 1962;
37.
e_1_2_1_24_3
Angew. Chem. internat. Edit. , 1963
38.
e_1_2_1_24_4
Olah G. A.
1963
39.
Alkylcarbonium- und Oxocarbonium-Salze
Olah G.A.
Angewandte Chemie , 1963
40.
e_1_2_1_24_6
Rev. Chim. Acad. Rep. Populaire Roumaine , 1962
41.
e_1_2_1_24_7
Prepr. Div. Petrol. Chem. Amer. Chem. Soc. , 1964
42.
e_1_2_1_24_8
1964
43.
Stable Carbonium Ions. V.1a Alkylcarbonium Hexafluoroantimonates
Olah G.A., Baker E.B., Evans J.C., Tolgyesi W.S., McIntyre J.S., Bastien I.J.
Journal of the American Chemical Society , 1964
47.
Fluorosulfuric acid and related superacid media
Gillespie R.J.
Accounts of Chemical Research , 1968
49.
Magic acid® [27b] is a registered trade mark of Cationics Inc. 653 Alpha Drive Cleveland Ohio 44 143 (USA) and is available together with other superacids and cationic reagents from this company as well as from Aldrich Chemical Co.
53.
Rapid rearrangements in the tert-amyl cation and the relative sign of the coupling constants
Saunders M., Hagen E.L.
Journal of the American Chemical Society , 1968
54.
Proton-13C Spin-Spin Coupling. V. Inadequacy of Correlation of Proton-13C Coupling with s-Character
Karabatsos G.J., Orzech C.E.
Journal of the American Chemical Society , 1964
55.
Stable carbonium ions. LXXXV. Laser Raman and infrared spectroscopic study of alkylcarbonium ions
Olah G.A., DeMember J.R., Commeyras A., Bribes J.L.
Journal of the American Chemical Society , 1971
56.
The Electronic Spectra of Carbonium Ions in Strongly Acidic Solutions1
Olah G.A., Pittman C.U., Waack R., Doran M.
Journal of the American Chemical Society , 1966
57.
e_1_2_1_36_2
Cheeseman T. P.
J. chem. Soc. (London)
58.
e_1_2_1_37_2
Zinke A.
Mh. Chem. , 1952
59.
X-ray photoelectron spectroscopy
Hollander J.M., Jolly W.L.
Accounts of Chemical Research , 1970
60.
ANALYTICAL POTENTIAL OF PHOTOELECTRON SPECTROSCOPY
Betteridge D., Baker A.D.
Analytical Chemistry , 1970
64.
Photoelectron spectroscopy of organic ions. I. Carbon 1s electron binding energies of the tert-butyl, trityl, and tropylium cations
Olah G.A., Mateescu G.D., Wilson L.A., Gross M.H.
Journal of the American Chemical Society , 1970
67.
e_1_2_1_40_2
Pochon M.
Trans. Amer. Inst. chem. Engr. , 1937
70.
Stable Carbonium Ions. XXVIII.1 Protonated Aliphatic Alcohols
Olah G.A., Namanworth E.
Journal of the American Chemical Society , 1966
71.
Stable carbonium ions. XLI. Protonated aliphatic alcohols and their cleavage to carbonium ions
Olah G.A., Sommer J., Namanworth E.
Journal of the American Chemical Society , 1967
72.
G. A.Olah J. M.Bollinger andP.Schilling to be published.
73.
Stable Carbonium Ions. XXXVI.1a Protonated Aliphatic Ethers and Their Cleavage to Carbonium Ions
Olah G.A., O'Brien D.H.
Journal of the American Chemical Society , 1967
74.
Stable carbonium ions. XL. Protonated aliphatic thiols and sulfides and their cleavage to carbonium ions
Olah G.A., O'Brien D.H., Pittman C.U.
Journal of the American Chemical Society , 1967
77.
G. A.OlahandP.Schilling to be published.
80.
The Solvolysis of p-Nitrobenzoates of Certain Cyclopropylcarbinols1,2
Hart H., Sandri J.M.
Journal of the American Chemical Society , 1959
81.
Physical Properties of the Tricyclopropylmethyl Cation
Deno N.C., Richey H.G., Liu J.S., Hodge J.D., Houser J.J., Wisotsky M.J.
Journal of the American Chemical Society , 1962
82.
G. A.OlahandP.Westerman to be published.
83.
Stable Carbonium Ions. XIV.1 Cyclopropylcarbonium Ions
Pittman C.U., Olah G.A.
Journal of the American Chemical Society , 1965
85.
Carbonium Ions. XI. Nuclear Magnetic Resonance Spectra of the Aliphatic Alkenyl Cations
Deno N.C., Richey H.G., Friedman N., Hodge J.D., Houser J.J., Pittman C.U.
Journal of the American Chemical Society , 1963
86.
Carbonium Ions. XIII. Ultraviolet Spectra and Thermodynamic Stabilities of Cycloalkenyl and Linear Alkenyl Cations
Deno N.C., Bollinger J., Friedman N., Hafer K., Hodge J.D., Houser J.J.
Journal of the American Chemical Society , 1963
87.
THE SYNTHESIS AND REACTIONS OF DIVINYL CARBONIUM IONS
Sorensen T.S.
Canadian Journal of Chemistry , 1964
88.
Stable Carbonium Ions. XII.1 Direct Observation of the Allyl and 2-Methylallyl Cations
Olah G.A., Comisarow M.B.
Journal of the American Chemical Society , 1964
91.
Stereochemistry of allyl cations from the isomeric 2,3-dimethylcyclopropyl chlorides. Stereomutations of allyl cations
Schleyer P.V., Su T.M., Saunders M., Rosenfeld J.C.
Journal of the American Chemical Society , 1969
92.
Stable carbonium ions. XCVI. Propadienylhalonium ions and 2-haloallyl cations
Bollinger J.M., Brinich J.M., Olah G.A.
Journal of the American Chemical Society , 1970
93.
e_1_2_1_65_2
Kern W.
Angew. Chem. , 1950
94.
e_1_2_1_66_2
Gabert A.
C. R. hebd. Séances Acad. Sci. , 1952
95.
The Preparation and Reactions of a Homologus Series of Aliphatic Polyenylic Cations
Sorensen T.S.
Journal of the American Chemical Society , 1965
96.
THE PREPARATION OF A TRIVINYL CARBONIUM ION
Sorensen T.S.
Canadian Journal of Chemistry , 1965
97.
Pentadienyl Cations and Their Rearrangements in FSO3H-SbF5Solution1
Olah G.A., Pittman C.U., Sorensen T.S.
Journal of the American Chemical Society , 1966
98.
Electronic Spectra of Carbonium Ions
Stuart A.A., Mackor E.L.
Journal of Chemical Physics , 1957
99.
The absorption spectra of aromatic carbonium ions in HF solution
Dallinga G., Mackor E.L., Verrijn Stuart A.A.
Molecular Physics , 1958
100.
N.m.r. study of proton exchange of weak bases in hydrogen fluoride
MacLean C., Mackor E.L.
Discussions of the Faraday Society , 1962
103.
e_1_2_1_71_3
Naturwissenschaften , 1956
105.
e_1_2_1_71_5
Olah G. A.
1960
106.
Stable Carbonium Ions. IX.1 Methylbenzenonium Hexafluoroantimonates2
Olah G.A.
Journal of the American Chemical Society , 1965
107.
Stable carbocations. CXXIV. Benzenium ion and monoalkylbenzenium ions
Olah G.A., Schlosberg R.H., Porter R.D., Mo Y.K., Kelly D.P., Mateescu G.D.
Journal of the American Chemical Society , 1972
108.
The 1,1,2,3,4,5,6-heptamethylbenzenonium ion
von E. Doering W., Saunders M., Boyton H.G., Earhart H.W., Wadley E.F., Edwards W.R., Laber G.
Tetrahedron , 1958
109.
G. A.Olah G. D.Mateescu andY. K.Mo J. Amer. Chem. Soc. in press.
110.
G. D.Mateescu Ph. D. Dissertation Case Western Reserve University 1971.
111.
Stable carbonium ions. XXXIV. 1-Methylcyclopentyl cation
Olah G.A., Bollinger J.M., Cupas C.A., Lukas J.
Journal of the American Chemical Society , 1967
112.
e_1_2_1_77_2
Schmidt M.
Angew. Chem. , 1959
114.
Stable carbocations. CXIV. Structure of cyclopropylcarbinyl and cyclobutyl cations
Olah G.A., Jeuell C.L., Kelly D.P., Porter R.D.
Journal of the American Chemical Society , 1972
115.
Ueber isomere Dehydrocamphersäuren, Lauronolsäuren und Bihydrolauro‐Lactone
Bredt J., Houben J., Levy P.
Berichte der deutschen chemischen Gesellschaft , 1902
118.
Direkte Synthese der Adamantan-carbonsäure-(1)
Koch H., Haaf W.
Angewandte Chemie , 1960
119.
Stable Carbonium Ions. VIII. The 1-Adamantyl Cation
Schleyer P.V., Fort R.C., Watts W.E., Comisarow M.B., Olah G.A.
Journal of the American Chemical Society , 1964
120.
G. A.Olah G. D.Mateescu G.Sipos andP. v. R.Schleyer J. Amer. Chem. Soc. in press.
121.
Stable Carbonium Ions. X.1 Direct Nuclear Magnetic Resonance Observation of the 2-Norbornyl Cation
Schleyer P.V., Watts W.E., Fort R.C., Comisarow M.B., Olah G.A.
Journal of the American Chemical Society , 1964
122.
e_1_2_1_86_2
Wilkinson G.
Naturwissenschaften , 1955
123.
e_1_2_1_86_3
Trippett S.
J. chem. Soc. (London)
124.
Ueber die basischen Eigenschaften des Kohlenstoffs und die Constitution des sogenannten Triphenylmethyls
Kehrmann F., Wentzel F.
Berichte der deutschen chemischen Gesellschaft , 1901
125.
e_1_2_1_87_3
Chem. Bet. , 1902
126.
Dibenzalaceton und Triphenylmethan. Ein Beitrag zur Farbtheorie
Baeyer A., Villiger V.
Berichte der deutschen chemischen Gesellschaft , 1902
127.
e_1_2_1_89_2
Gold V.
J. Chem. Soc.
130.
Carbonium Ions. XV.1 Observation of “Classical” Phenylethyl Cations
Olah G.A., Pittman C.U.
Journal of the American Chemical Society , 1965
131.
Stable Carbonium Ions. XXII.1a Phenylethyl Cations2
Olah G.A., Pittman C.U., Namanworth E., Comisarow M.B.
Journal of the American Chemical Society , 1966
132.
Stable Carbonium Ions. XIX.1 Benzyl Cations
Cupas C.A., Comisarow M.B., Olah G.A.
Journal of the American Chemical Society , 1966
133.
Stable carbonium ions. XLV. Benzyl cations
Bollinger J.M., Comisarow M.B., Cupas C.A., Olah G.A.
Journal of the American Chemical Society , 1967
134.
Stable carbonium ions. CXI. Styryl(1-phenylethyl) cation and substituted styryl cations
Olah G.A., Porter R.D., Kelly D.P.
Journal of the American Chemical Society , 1971
135.
A STABLE DIPOSITIVE CARBONIUM ION1
Hart H., Fish R.W.
Journal of the American Chemical Society , 1958
136.
A Stable Dipositive Carbonium Ion1,2
Hart H., Fish R.W.
Journal of the American Chemical Society , 1960
137.
Multicharged Carbonium Ions. III. Long-lived Ions from Trichloromethylpolymethylbenzenes1-3
Hart H., Fish R.W.
Journal of the American Chemical Society , 1961
138.
On the Supposed Formation of Extraordinary Dipositive Carbonium Ions in Sulfuric Acid
Gillespie R.J., Robinson E.A.
Journal of the American Chemical Society , 1964
139.
The Supposed ArC2+Cl Ions
Deno N.C., Friedman N., Mockus J.
Journal of the American Chemical Society , 1964
140.
On Carbonium Ions in Chlorosulfuric Acid
Robinson E.A., Ciruna J.A.
Journal of the American Chemical Society , 1964
141.
Tetraphenylcyclobutadiene Derivatives. V.1 The Tetraphenylcyclobutenium Dication
Freedman H.H., Frantz A.M.
Journal of the American Chemical Society , 1962
143.
Stable carbonium ions. LXXXIX. Tetramethylcyclobutenium dication, an aromatic 2 .pi.-electron system
Olah G.A., Bollinger J.M., White A.M.
Journal of the American Chemical Society , 1969
144.
Stable carbonium ions. CI. Tetraphenylcyclobutadiene dication
Olah G.A., Mateescu G.D.
Journal of the American Chemical Society , 1970
145.
The sym-Triphenylcyclopropenyl Cation, a Novel Aromatic System1
Breslow R., Yuan C.
Journal of the American Chemical Society , 1958
146.
Cyclopropenyl cation
Breslow R., Groves J.T., Ryan G.
Journal of the American Chemical Society , 1967
147.
Dicarbonium Ions of the Triarylmethyl Type. Ions from o-, m- and p- Xylylene Glycols
Hart H., Sulzberg T., Rafos R.R.
Journal of the American Chemical Society , 1963
148.
e_1_2_1_107_2
Volz H.
Tetrahedron Lett.
149.
e_1_2_1_107_3
Angew. Chem. internat. Edit. , 1962
150.
Stable Carbonium Ions. XXXII.1 Alkyldicarbonium Ions
Bollinger J.M., Cupas C.A., Friday K.J., Woolfe M.L., Olah G.L.
Journal of the American Chemical Society , 1967
151.
Ueber Tropin
Merling G.
Berichte der deutschen chemischen Gesellschaft , 1891
152.
The Cycloheptatrienylium (Tropylium) Ion
Von E.Doering W., Knox L.H.
Journal of the American Chemical Society , 1954
153.
SYNTHESIS OF TROPENIUM (CYCLOHEPTATRIENYLIUM) SALTS BY HYDRIDE EXCHANGE1
Dauben H.J., Gadecki F.A., Harmon K.M., Pearson D.L.
Journal of the American Chemical Society , 1957
154.
Stable Carbonium Ions. XX.1 Phenyl- and Diphenylfluorocarbonium Ions
Olah G.A., Cupas C.A., Comisarow M.B.
Journal of the American Chemical Society , 1966
155.
(a) For a summary seeG. A.OlahandY. K.Mo Advan. Fluorine Chem. in press;
156.
(b)G. A.OlahandY. K.MoinG. A. OlahandP. v. R. Schleyer:Carbonium Ions. Wiley‐Interscience New York Vol. 5 in press.
157.
Stable Carbonium Ions. XXXVII.1 Alkyl- and Arylalkylfluorocarbonium Ions. The Dimethyl- and Phenylmethylfluorocarbonium Ion
Olah G.A., Chambers R.D., Comisarow M.B.
Journal of the American Chemical Society , 1967
159.
Stable Carbonium Ions. XXXV.1 Pentafluorophenylcarbonium Ions
Olah G.A., Comisarow M.B.
Journal of the American Chemical Society , 1967
160.
Tris(pentafluorophenyl)methyl Cation
Filler R., Wang C., McKinney M.A., Miller F.N.
Journal of the American Chemical Society , 1967
161.
Fluorocyclopropanes. II. Synthesis, properties, and reactions of perfluorocyclopropene
Sargeant P.B., Krespan C.G.
Journal of the American Chemical Society , 1969
162.
e_1_2_1_119_2
Hallam B. F.
J. Chem. Soc.
163.
e_1_2_1_119_3
Tetrahedron Lett.
164.
e_1_2_1_120_2
Ballester M.
Tetrahedron Lett.
165.
Pentachloroallyl Cation and Its Salts1
West R., Kwitowski P.T.
Journal of the American Chemical Society , 1966
166.
Stable carbonium ions. LXXXI. Alkyl(aryl)halocarbonium ions and haloarylcarbonium ions
Olah G.A., Comisarow M.B.
Journal of the American Chemical Society , 1969
169.
stable carbonium ions. lvii catalysts with olefins.ang. .ang.
Olah G.A., Bollinger J.M.
Journal of the American Chemical Society , 1968
172.
Friedel-Crafts chemistry. IV. Dialkylhalonium ions and their possible role in Friedel-Crafts reactions
Olah G.A., DeMember J.R.
Journal of the American Chemical Society , 1969
174.
e_1_2_1_127_2
Samartzewa A. G.
Trav. Inst. État Radium , 1938
175.
LXVI.—The salts of dimethylpyrone, and the quadrivalence of oxygen
Collie J.N., Tickle T.
Journal of the Chemical Society Transactions , 1899
177.
Über die Natur der Halogenwasserstoffe
Hantzsch A.
Berichte der deutschen chemischen Gesellschaft (A and B Series) , 1925
178.
Meerwein H., Bodenbenner K., Borner P., Kunert F., Wunderlich K.
1960
179.
Meerwein H., Hederich V., Morschel H., Wunderlich K.
1960
180.
The Spectral Properties of Alkoxymethyl Cations1
Ramsey B.G., Taft R.W.
Journal of the American Chemical Society , 1966
181.
Stable carbonium ions. XXXIII. Primary alkoxycarbonium ions
Olah G.A., Bollinger J.M.
Journal of the American Chemical Society , 1967
182.
Nuclear Magnetic Resonance of Proton Complexes of Weak Bases
MacLean C., Mackor E.L.
Journal of Chemical Physics , 1961
186.
O-H Chemical Shift, Conformation, and Electron Delocalization in Protonated Carbonyl Compounds
Brookhart M., Levy G.C., Winstein S.
Journal of the American Chemical Society , 1967
187.
Stable carbonium ions. XLII. Protonated aliphatic aldehydes
Olah G.A., O'Brien D.H., Calin M.
Journal of the American Chemical Society , 1967
188.
Stable carbonium ions. XLIII. Protonated aliphatic ketones
Olah G.A., Calin M., O'Brien D.H.
Journal of the American Chemical Society , 1967
192.
Stable carbonium ions. LII. Protonated esters and their cleavage in fluorosulfonic acid-antimony pentafluoride solution
Olah G.A., O'Brien D.H., White A.M.
Journal of the American Chemical Society , 1967
194.
e_1_2_1_140_4
Hogeveen H.
Chem. Commun.
195.
Chemistry and spectroscopy in strongly acidic solutions. Part III: Formation of two different entities on protonation of formic acid
Hogeveen H., Bickel A.F., Hilbers C.W., Mackor E.L., Maclean C.
Recueil des Travaux Chimiques des Pays-Bas , 2010
199.
e_1_2_1_143_3
Cook D.
1963
203.
e_1_2_1_145_4
Olah G. A.
Rev. Chim. Acad. Rep. Populaire Roumaine , 1962
205.
The Crystal Structure of CH3CO+SbF6-
Boer F.P.
Journal of the American Chemical Society , 1966
206.
Stable Carbonium Ions. XXVII.1a Cyclo- and Polycycloalkyloxocarbonium Ions
Olah G.A., Comisarow M.B.
Journal of the American Chemical Society , 1966
207.
Stable Carbonium Ions. XXV.1a Alkylene- (Arylene-) dioxodicarbonium Ions (Acyl Dications)
Olah G.A., Comisarow M.B.
Journal of the American Chemical Society , 1966
208.
Stable carbonium ions. XXXVIII. Alkenyloxocarbonium ions
Olah G.A., Comisarow M.B.
Journal of the American Chemical Society , 1967
210.
e_1_2_1_153_2
Armstrong V. C.
Chem. Commun.
213.
e_1_2_1_156_2
Sudmeier J. L.
Chem. Commun.
214.
Stable carbonium ions. LXIX. Protonation of ureas, guanidines, and biotin in super acid solution
Olah G.A., White A.M.
Journal of the American Chemical Society , 1968
216.
Über Nitriliumsalze, I. Mitteil.
Meerwein H., Laasch P., Mersch R., Spille J.
Chemische Berichte , 1956
217.
Triazidocarbonium-hexachloroantimonat [C(N3)3]+ [SbCl6]−
Müller U., Dehnicke K.
Angewandte Chemie , 1966
218.
e_1_2_1_160_3
Angew. Chem. internat. Edit. , 1966
219.
Protonated heteroaliphatic compounds
Olah G.A., White A.M., O'Brien D.H.
Chemical Reviews , 1970
220.
Rearrangement reactions of secondary carbonium ions. Protonated cyclopropane intermediates formed from sec-butyl cation
Saunders M., Hagen E.L., Rosenfeld J.
Journal of the American Chemical Society , 1968
221.
Stable Carbonium Ions. XI.1 The Rate of Hydride Shifts in the 2-Norbornyl Cation
Saunders M., Schleyer P.V., Olah G.A.
Journal of the American Chemical Society , 1964
222.
e_1_2_1_164_2
Natta G.
Chem. and Ind. (London)
223.
Degenerate five-carbon scrambling in the 7-norbornadienyl cation
Lustgarten R.K., Brookhart M., Winstein S.
Journal of the American Chemical Society , 1967
224.
Structure of the Nonclassical 7-Norbornenyl Cation1
Brookhart M., Diaz A., Winstein S.
Journal of the American Chemical Society , 1966
225.
Direct Observation of Norbornenyl Cations
Richey H.G., Lustgarten R.K.
Journal of the American Chemical Society , 1966
226.
Structure of the 7-Norbornadienyl Carbonium Ion
Story P.R., Saunders M.
Journal of the American Chemical Society , 1962
227.
A Detailed Analysis of the 7-Norbornadienyl Carbonium Ion Nuclear Magnetic Resonance Spectrum
Story P.R., Snyder L.C., Douglass D.C., Anderson E.W., Kornegay R.L.
Journal of the American Chemical Society , 1963
228.
THE STRUCTURE OF THE BICYCLO[2,2,1]2-HEPTYL (NORBORNYL) CARBONIUM ION
Winstein S., Trifan D.S.
Journal of the American Chemical Society , 1949
229.
On Brown's Classical Norbornyl Cation
Winstein S.
Journal of the American Chemical Society , 1965
231.
Small-ring Compounds. XXIII. The Nature of the Intermediates in Carbonium Ion-type Interconversion Reactions of Cyclopropylcarbinyl, Cyclobutyl and Allylcarbinyl Derivatives1a
Mazur R.H., White W.N., Semenow D.A., Lee C.C., Silver M.S., Roberts J.D.
Journal of the American Chemical Society , 1959
233.
Stereochemistry of the cyclopropylcarbinyl-cyclopropylcarbinyl rearrangement
Wiberg K.B., Szeimies G.
Journal of the American Chemical Society , 1968
234.
for a review seeK. B.Wiberg B. A.Hess Jr. andA. J.Ashe IIIinG. A. OlahandP. v. R. Schleyer:Carbonium Ions. Wiley‐Interscience New York Vol. 3 in press.
237.
Stable carbonium ions. XXXI. p-Anisonium and methylphenonium ion-formation via aryl participation in strong acid solution
Olah G.A., Comisarow M.B., Namanworth E., Ramsey B.G.
Journal of the American Chemical Society , 1967
239.
Stable carbonium ions. CXV. Ethylenephenonium and ethylene-p-toluonium ions
Olah G.A., Porter R.D.
Journal of the American Chemical Society , 1970
241.
e_1_2_1_173_2
Ingold C. K.
1959
242.
e_1_2_1_173_3
Olah G. A.
1963
243.
e_1_2_1_173_4
Bethell D.
1967
244.
(d)G. A.OlahandP. v. R.Schleyer:Carbonium Ions. Wiley‐Interscience New York1968–1972 Vol. 1–3 Vol. 4 in press.
245.
e_1_2_1_174_2
Talroze V. L.
Dokl. Akad. Nauk SSSR , 1952
246.
Reactions of Gaseous Ions. XIV. Mass Spectrometric Studies of Methane at Pressures to 2 Torr
Field F.H., Munson M.S.
Journal of the American Chemical Society , 1965
248.
e_1_2_1_175_5
Hogeveen H.
Chem. Commun.
250.
Electrophilic Substitution at methane: Short communication
Hogeveen H., Gaasbeek C.J.
Recueil des Travaux Chimiques des Pays-Bas , 2010
252.
An investigation of the geometry of the CH+5 ion by the CNDO method
Gamba A., Morosi G., Simonetta M.
Chemical Physics Letters , 1969
254.
The electronic structure and stability of CH+5 and CH−5
Mulder J.J., Wright J.S.
Chemical Physics Letters , 1970
256.
Near hartree-fock energy and equilibrium geometry of CH+5
Dyczmons V., Staemmler V., Kutzelnigg W.
Chemical Physics Letters , 1970
257.
(b)A.DedieuandA.Veillard Lecture at 21st Annual Meeting of the Société Chimique Physique Paris Sept. 1970;
258.
A.Veillard personal communication;
259.
e_1_2_1_178_5
Lathan W. A.
Tetrahedron Lett.
261.
Topological representation of stereoisomerism. I. Polytopal rearrangements
Muetterties E.L.
Journal of the American Chemical Society , 1969
262.
The Hydrolysis of Aqueous Hydroborate
Mesmer R.E., Jolly W.L.
Inorganic Chemistry , 1962
264.
e_1_2_1_182_2
Well A. N.
J. Chem. Phys. , 1946
268.
G. A.Olah R.Renner andP.Schilling to be published.
269.
G. A.OlahandG. D.Mateescu 159th Nat. Meet. Amer. Chem. Soc. Houston Texas Feb.1970 Abstr. Papers.
270.
Mechanisms for carbon–hydrogen bond breakage
Lewis E.S., Symons M.C.
Quarterly Reviews Chemical Society , 1958
271.
Amine Boranes. III. Hydrolysis of Pyridine Diphenylborane and the Mechanism of Hydride Transfer Reactions
Hawthorne M.F., Lewis E.S.
Journal of the American Chemical Society , 1958
273.
e_1_2_1_190_2
Hogeveen H.
Rev. Trav. Chim. Pays‐Bas , 1969
274.
Electrophilic Substitutions at Alkanes and in Alkylcarbonium Ions
Brouwer D.M., Hogeveen H.
Progress in Physical Organic Chemistry , 1972
275.
e_1_2_1_191_2
Bickel A. F.
Chem. Commun.
277.
The Mechanism of the Alkylation of Paraffins
Schmerling L.
Journal of the American Chemical Society , 1945
278.
THE MECHANISM OF PARAFFIN ISOMERIZATION
Bloch H.S., Pines H., Schmerling L.
Journal of the American Chemical Society , 1946
279.
Exchanges of Halogen and Hydrogen between Organic Halides and Isoparaffins in the Presence of Aluminum Halides
Bartlett P.D., Condon F.E., Schneider A.
Journal of the American Chemical Society , 1944
280.
e_1_2_1_193_3
Nenitzescu C. D.
Bull. Soc. chim. France
284.
Electron Deficient Compounds1
Rundle R.E.
Journal of the American Chemical Society , 1947
286.
e_1_2_1_198_2
Pines H.
1964
287.
Durch Aluminiumchlorid Katalysierte Reaktion, VI. Mitteil.: Die Umlagerung des Cyclohexans in Metyl‐cyclopentan
Nenitzescu C.D., Cantuniari I.P.
Berichte der deutschen chemischen Gesellschaft (A and B Series) , 1933
288.
e_1_2_1_199_3
Nenitzescu C. D.
Bull. Soc. chim. France
292.
Stereochemical inhibition of intramolecular 1,2 shifts. Intermolecular nature of hydride shifts in the adamantane series
Schleyer P.V., Lam L.K., Raber D.J., Fry J.L., McKervey M.A., Alford J.R., Cuddy B.D., Keizer V.G., Geluk H.W., Schlatmann J.L.
Journal of the American Chemical Society , 1970
294.
Carbonium Ions. X. Hydride Transfers Involving Arylcarbonium and Alkylcarbonium Ions
Deno N., Saines G., Spangler M.
Journal of the American Chemical Society , 1962
295.
e_1_2_1_205_3
Stewart R.
1966
296.
HEPTALENIUM ION
Dauben H.J., Bertelli D.J.
Journal of the American Chemical Society , 1961
297.
e_1_2_1_207_3
Harmon K. M.
1972
298.
Experimental results supporting this suggestion were recently reported byG. A.OlahandJ. J.Svoboda Manchester Meeting of the Chemical Society April 1972;
299.
J. Amer. Chem. Soc. in press.
300.
e_1_2_1_209_2
Lankamp H.
Tetrahedron Lett.
301.
e_1_2_1_210_2
Razuvaev G. A.
Doklady Akad. Nauk. SSSR , 1957
303.
e_1_2_1_211_3
Dewar M. J. S.
J. Chem. Soc.
304.
e_1_2_1_211_4
Bull. Soc. chim. France
305.
For theoretical aspects seeL.Radom J. A.Pople V.Buss andP. v. R.Schleyer J. Amer. Chem. Soc. in press.
306.
Vertical stabilization of cations by neighboring .sigma. bonds. General considerations
Traylor T.G., Hanstein W., Berwin H.J., Clinton N.A., Brown R.S.
Journal of the American Chemical Society , 1971
307.
Modes of carbonium ion stabilization. Evidence from charge-transfer spectra
Hanstein W., Berwin H.J., Traylor T.G.
Journal of the American Chemical Society , 1970
308.
Organometallic chemistry. I. Ethylene- and norbornylenemercurinium ions
Olah G.A., Clifford P.R.
Journal of the American Chemical Society , 1971
309.
e_1_2_1_216_2
Natta G.
Chim. e. Ind. (Milan) , 1958
310.
G. A.Olahet al. to be published.
311.
e_1_2_1_218_2
Brown H. C.
1962
312.
e_1_2_1_219_2
Lehmkuhl H.
1970
313.
A Correlation of Reaction Rates
Hammond G.S.
Journal of the American Chemical Society , 1955
315.
G. A.Olah H.Lin andY. K.Mo to be published.
316.
e_1_2_1_223_2
Hallam B. F.
J. Chem. Soc.
317.
e_1_2_1_223_3
Bull. Soc. chim. France
318.
e_1_2_1_223_4
1949
319.
Physical Organic Chemistry: II-Complexes as Intermediates in Organic Reactions
Dewar M.J., Marchand A.P.
Annual Review of Physical Chemistry , 1965
320.
e_1_2_1_225_2
Ingold C. K.
1969
321.
Retention of Configuration in the Reaction of the 3-Bromo-2-butanols with Hydrogen Bromide
Winstein S., Lucas H.J.
Journal of the American Chemical Society , 1939
322.
The Halogenation of Ethylenes
Roberts I., Kimball G.E.
Journal of the American Chemical Society , 1937
323.
e_1_2_1_227_2
Schlögel K.
Österr. Chemiker‐Ztg. , 1958
324.
Rearrangement of Alkyl Groups. Kinetic and Tracer Studies in the Pinacol Rearrangement1
Stiles M., Mayer R.P.
Journal of the American Chemical Society , 1959
325.
The Stereochemistry of the Perbenzoic Acid Oxidation of Optically Active exo-Acetylnorbornane1
Berson J.A., Suzuki S.
Journal of the American Chemical Society , 1959
326.
Molecular orbital calculations on carbonium ions. III. Barriers in ethyl cations
Williams J.E., Buss V., Allen L.C., Schleyer P.V., Lathan W.A., Hehre W.J., Pople J.A.
Journal of the American Chemical Society , 1970
327.
Activated complex for hydrogen migration in the ethyl cation. Ab initio calculations
Pfeiffer G.V., Jewett J.G.
Journal of the American Chemical Society , 1970
328.
The Atom and the Molecule
Lewis G.N.
Journal of the American Chemical Society , 1916
329.
e_1_2_1_232_3
1963