Home / Articles / Catalysis of Symmetry-disallowed Reactions

Catalysis of Symmetry-disallowed Reactions

Veronika Iosifovna Labunskaya 1
Veronika Iosifovna Labunskaya
, 
Asya Dmitrievna Shebaldova 1
Asya Dmitrievna Shebaldova
, 
Mikhail L'vovich Khidekel' 2
Mikhail L'vovich Khidekel'
1 Saratov State University named after N. G. Chernyshevsky
2 Institute of Chemical Physics of the USSR Academy of Sciences, Moscow
Published 30 November 1973
Communication , Volume 43, Issue 1, 1-16
8
Share
Cite this
GOST
 | 
Cite this
GOST
Labunskaya V. I., Shebaldova A. D., Khidekel' M. L. Catalysis of Symmetry-disallowed Reactions // Russian Chemical Reviews. 1974. Vol. 43. No. 1. pp. 1-16.
GOST all authors (up to 50)
Labunskaya V. I., Shebaldova A. D., Khidekel' M. L. Catalysis of Symmetry-disallowed Reactions // Russian Chemical Reviews. 1974. Vol. 43. No. 1. pp. 1-16.
RIS
 | 
Cite this
RIS
TY - JOUR
DO - 10.1070/RC1974v043n01ABEH001785
UR - https://rcr.colab.ws/publications/10.1070/RC1974v043n01ABEH001785
TI - Catalysis of Symmetry-disallowed Reactions
T2 - Russian Chemical Reviews
AU - Labunskaya, Veronika Iosifovna
AU - Shebaldova, Asya Dmitrievna
AU - Khidekel', Mikhail L'vovich
PY - 1974
DA - 1973/11/30
PB - ANO Editorial Board of the journal Uspekhi Khimii
SP - 1-16
IS - 1
VL - 43
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors)
@article{1974_Labunskaya,
author = {Veronika Iosifovna Labunskaya and Asya Dmitrievna Shebaldova and Mikhail L'vovich Khidekel'},
title = {Catalysis of Symmetry-disallowed Reactions},
journal = {Russian Chemical Reviews},
year = {1974},
volume = {43},
publisher = {ANO Editorial Board of the journal Uspekhi Khimii},
month = {Nov},
url = {https://rcr.colab.ws/publications/10.1070/RC1974v043n01ABEH001785},
number = {1},
pages = {1--16},
doi = {10.1070/RC1974v043n01ABEH001785}
}
MLA
Cite this
MLA
Labunskaya, Veronika Iosifovna, et al. “Catalysis of Symmetry-disallowed Reactions.” Russian Chemical Reviews, vol. 43, no. 1, Nov. 1974, pp. 1-16. https://rcr.colab.ws/publications/10.1070/RC1974v043n01ABEH001785.
Views / Visits / Downloads
29 / 29 / 12

Abstract

Opportunities for applying the principle of the conservation of orbital symmetry to catalytic processes are surveyed. Current views on the role of a transition metal in the catalysis of symmetry-disallowed reactions are reported, and possible mechanisms are discussed. Close attention is paid to the correlation of the catalytic activity of metal-containing catalysts with the electron configuration of the transition metal, the structure of the complex, and the nature of the ligands. Examples of catalytic reactions disallowed by the Woodward–Hoffmann rules – valency isomerisation of hydrocarbons, hydrogenation and disproportionation of alkenes, cyclo-oligomerisation – are considered in the light of ideas on concerted and stepwise mechanisms. A list of 137 references is included.

References

2.
Selection Rules for Concerted Cycloaddition Reactions
Hoffmann R., Woodward R.B.
Journal of the American Chemical Society , 1965
3.
Selection Rules for Sigmatropic Reactions
Woodward R.B., Hoffmann R.
Journal of the American Chemical Society , 1965
4.
The Form of d Orbitals in Carbon-Sulfur π Bonds1
Goodman L., Taft R.W.
Journal of the American Chemical Society , 1965
5.
Orbital Symmetries and Orientational Effects in a Sigmatropic Reaction
Hoffmann R., Woodward R.B.
Journal of the American Chemical Society , 1965
6.
6
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1953
7.
7
E. Rabinowitch
"Photosynthesis" , 1956
8.
8
V. N. Kondrat'ev
"Kinetika Reaktsii v Gazovoi Faze" (Kinetics of Reactions in the Gas Phase) , 1959
9.
9
V. H. Lynch
Carnegie Inst. Year Book , 1954
10.
10
T. A. Kryukova
"Polyaro-graficheskii Analiz" (Polarographic Analysis) , 1959
11.
Woodward-Hoffmann rules: Cycloaddition reactions
Vollmer J.J., Servis K.L.
Journal of Chemical Education , 1970
12.
Stereoselection in the Elementary steps of Organic Reactions
Miller S.I.
Advances in Physical Organic Chemistry , 1968
13.
Molecular rearrangements related to the Claisen rearrangement
Jefferson A., Scheinmann F.
Quarterly Reviews Chemical Society , 1968
14.
14
V. B. Evstigneev
Zhur. Fiz. Khim. , 1958
15.
15
A. S. Holt
"Research in Photosynthesis" , 1957
16.
A Molecular Orbital Theory of Reactivity in Aromatic Hydrocarbons
Fukui K., Yonezawa T., Shingu H.
Journal of Chemical Physics , 1952
17.
Theory of Substitution in Conjugated Molecules
Fukui K., Yonezawa T., Nagata C.
Bulletin of the Chemical Society of Japan , 1954
18.
The electronic structure of conjugated systems I. General theory
COULSON C A, LONGUET-HIGGINS H C
Proceedings of the Royal Society A: Mathematical, Physical and Engineering Sciences , 1947
19.
The electronic structure of conjugated systems II. Unsaturated hydrocarbons and their hetero-derivatives
Proceedings of the Royal Society A: Mathematical, Physical and Engineering Sciences , 1947
20.
Allyl Polymerization. II. Decomposition of Benzoyl Peroxide in Allyl Esters1,2
Gaylord N.G., Eirich F.R.
Journal of the American Chemical Society , 1952
21.
21
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1958
22.
22
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1958
23.
Dissociation of excited diatomic molecules by external perturbations
Proceedings of the Royal Society of London Series A Containing Papers of a Mathematical and Physical Character , 2006
25.
25
G. W. Robinson
J. Chem. Phys. , 1955
26.
26
B. Ya. Dain
1957
27.
Molecular orbital symmetry conservation in transition metal catalyzed transformations
Mango F.D., Schachtschneider J.H.
Journal of the American Chemical Society , 1967
28.
28
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1955
30.
Orbital symmetry restraints to transition metal catalyzed [2+2] cycloaddition reactions
Mango F.D., Schachtschneider J.H.
Journal of the American Chemical Society , 1971
34.
34
G. W. Robinson
J. Chem. Phys. , 1886
35.
Catalysis of symmetry-restricted reactions by transition metal compounds. Valence isomerization of cubane
Cassar L., Eaton P.E., Halpern J.
Journal of the American Chemical Society , 1970
37.
Catalysis of strained .sigma. bond rearrangements by silver(I) ion
38.
Thermal and silver ion catalyzed isomerization of the 1,1′-bishomocubane system: preparation of a new C10H10isomer
Dauben W.G., Buzzolini M.G., Schallhorn C.H., Whalen D.L., Palmer K.J.
Tetrahedron Letters , 1970
42.
Ag+-catalysed rearrangements of seco-cubane derivatives
Westberg H.H., Ona H.
Journal of the Chemical Society D Chemical Communications , 1971
44.
Oxidation of 1-methylcyclobutene by metal ions
Byrd J.E., Cassar L., Eaton P.E., Halpern J.
Journal of the Chemical Society D Chemical Communications , 1971
45.
Transition metal catalysis of symmetry forbidden reactions; a linear free energy correlation
Koser G.F.
Journal of the Chemical Society D Chemical Communications , 1971
46.
47
G. Oster
"Research in Photosynthesis" , 1957
47.
Valence isomerization of quadricyclene to norbornadiene catalyzed by transition metal complexes
Hogeveen H., Volger H.C.
Journal of the American Chemical Society , 1967
49.
50
G. Glacomello
Gazzetta. , 1935
50.
51
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1954
51.
Silver(I)-catalyzed conversion of bicyclobutanes to butadienes. Concerning stereospecificity
Sakai M., Yamaguchi H., Westberg H.H., Masamune S.
Journal of the American Chemical Society , 1971
54.
Palladium(II)-catalysed isomerization of bicyclobutanes
Sakai M., Yamaguuchi H., Masamune S.
Journal of the Chemical Society D Chemical Communications , 1971
55.
Ligand dependency in the transition-metal-promoted rearrangements of derivatives of bicyclo[1,1,0]butane
Gassman P.G., Meyer G.R., Williams F.J.
Journal of the Chemical Society D Chemical Communications , 1971
58.
Silver(I) ion catalyzed rearrangements of strained .sigma. bonds. IV. Fate of tricyclo[4.1.0.02,7]heptane
Paquette L.A., Allen G.R., Henzel R.P.
Journal of the American Chemical Society , 1970
60.
Evidence for stepwise bond cleavage in the transition metal promoted isomerizations of simple bicyclo[1,1,0]butanes
Gassman P.G., Williams F.J.
Journal of the Chemical Society Chemical Communications , 1972
61.
Thermal rearrangement of tricyclo[4.1.0.02,7]heptane
Wiberg K.B., Szeimies G.
Tetrahedron Letters , 1968
62.
The Specificity of Metal Catalysts in the Opening of Highly Strained Polycyclic Molecules
Gassman P.G., Atkins T.J.
Journal of the American Chemical Society , 1971
63.
Transition metal promoted isomerizations of highly strained polycyclic systems. Mechanistic insight
67.
Oxidative degradation of (benzocyclobutadiene)iron tricarbonyl
Merk W., Pettit R.
Journal of the American Chemical Society , 1967
69.
Thermal and catalysed rearrangement of olefinic epoxides
Grigg R., Shelton G.
Journal of the Chemical Society D Chemical Communications , 1971
70.
Rhodium(I) catalysed rearrangements of cyclo-octatetraene epoxide and bicyclo[6,1,0]nonatrienes
Grigg R., Hayes R., Sweeney A.
Journal of the Chemical Society D Chemical Communications , 1971
71.
Olefin Disproportionation
Bailey G.C.
Catalysis Reviews - Science and Engineering , 1970
72.
75
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1950
73.
Catalytic Disproportionation of Unsaturated Hydrocarbons
Khidekel' M.L., Shebaldova A.D., Kalechits I.V.
Russian Chemical Reviews , 1971
77.
The mechanism of propylene disproportionation
Clark A., Cook C.
Journal of Catalysis , 1969
78.
Olefin metathesis. I. Acyclic vinylenic hydrocarbons
Calderon N., Ofstead E.A., Ward J.P., Judy W.A., Scott K.W.
Journal of the American Chemical Society , 1968
80.
Kinetics and mechanism of the homogeneous olefin disproportionation reaction
81.
84
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1947
82.
85
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1947
84.
Mechanism of the metal-catalyzed disproportionation of olefins
Lewandos G.S., Pettit R.
Journal of the American Chemical Society , 1971
85.
Possible intermediate in the tungsten-catalyzed olefin metathesis reaction
Grubbs R.H., Brunck T.K.
Journal of the American Chemical Society , 1972
86.
Rhodium(I)-catalysed dismutation of electron-rich olefins: rhodium(I) carbene complexes as intermediates
Cardin D.J., Doyle M.J., Lappert M.F.
Journal of the Chemical Society Chemical Communications , 1972
87.
90
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1951
88.
91
L. M. Vorob'eva
Biokhimiya , 1956
89.
Homogeneous Hydrogenation
Vol'pin M.E., Kolomnikov I.S.
Russian Chemical Reviews , 1969
90.
Hydrogenation of organic compounds using homogeneous catalysts
Harmon R.E., Gupta S.K., Brown D.J.
Chemical Reviews , 1973
91.
94
A. A. Krasnovskii
Fiziologiya Rastenii , 1957
92.
molecular orbital symmetry rules
PEARSON R.G.
Chemical & Engineering News , 1970
93.
Symmetry rules for chemical reactions
Pearson R.G.
Accounts of Chemical Research , 1971
94.
97
A. N. Terenin
Dokl. Akad. Nauk SSSR , 1952
95.
98
W. Franke
Chem. Zentr. , 1954
98.
Catalytic Hydrogenation of Organic Compounds by Pentacyanocobaltate(II)
Kwiatek J., Mador I.L., Seyler J.K.
Journal of the American Chemical Society , 1962
99.
Catalytic Hydrogenation by Pentacyanocobaltate(II)
KWIATEK J., MADOR I.L., SEYLER J.K.
Photochemistry and Radiation Chemistry , 1962
100.
103
L. N. Bell
Dokl. Akad. Nauk SSSR , 1956
101.
104
O. P. Osipova
Dokl. Akad. Nauk SSSR , 1950
102.
105
F. F. Litvin
Dokl. Akad. Nauk SSSR , 1958
103.
106
F. Fichter
Helv. Chim. Acta , 1927
104.
107
M. F. Shostakovskii
Zhur. Obshch. Khim. , 1961
105.
108
F. Fichter
Helv. Chim. Acta , 1924
107.
110
M. F. Shostakovskii
Dokl. Akad. Nauk SSSR , 1960
108.
111
M. Calvin
1956
109.
112
A. G. Pozdeeva
Zhur. Prikl. Khim. , 1952
110.
113
H. Blum
"Photodynamic Action and Diseases caused Light" , 1940
111.
114
L. Segal
"Chemical Reactions of Polymers" , 1964
112.
115
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1957
113.
116
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1957
114.
117
V. V. Levchenko
Zhur. Obshch. Khim. , 1948
115.
118
V. M. Rodionov
Zhur. Obshch. Khim. , 1935
116.
119
V. V. Levchenko
Zhur. Obshch. Khim. , 1947
118.
Catalytic Hydrogenation and Hydrogenolysis by Pentacyanocobaltate(II)
KWIATEK J., SEYLER J.K.
Photochemistry and Radiation Chemistry , 1974
119.
Preparation of organocyanocobaltate(III) complexes
Kwiatek J., Seyler J.K.
Journal of Organometallic Chemistry , 1965
120.
The hydrogenation of buta-1,3-diene catalysed by potassium pentacyanocobaltate(II)
Burnett M.G., Connolly P.J., Kemball C.
Journal of the Chemical Society A Inorganic Physical Theoretical , 1968
124.
127
R. Pasternak
Helv. Chim. Acta , 1948
126.
129
J. Wiemann
Bull. Soc. chim. France , 1955
127.
Reduction of Water to Hydrogen by a Complex Cyanide of Cobalt
King N.K., Winfield M.E.
Journal of the American Chemical Society , 1958
128.
Catalytic Activation of Molecular Hydrogen by Cobalt Cyanide Solutions
Mills G.A., Weller S., Wheeler A.
The Journal of Physical Chemistry , 1959
129.
The Liquid Phase Hydrogenation of Cyanocobaltate(II)
King N.K., Winfield M.E.
Journal of the American Chemical Society , 1961
130.
Hydrierung von 1-hepten mit RhX(CO)L2 als funktion von X und L
Strohmeier W., Rehder-Stirnweiss W.
Journal of Organometallic Chemistry , 1969
131.
Ligandenaustausch in den hydrierungskatalysatoren IrX(CO)L2 und RhX(CO)L2
Strohmeier W., Rehder-Stirnweiss W., Reischig G.
Journal of Organometallic Chemistry , 1971
132.
Homogeneous catalytic hydrogenation of unsaturated organic compounds
Harmon R.E., Parsons J.L., Cooke D.W., Gupta S.K., Schoolenberg J.
Journal of Organic Chemistry , 1969
136.
Katalytische Hydrierung von Olefinen mit RhX(CO)L2
Strohmeier W., Rehder-Stirnweiss W.
Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences , 1969
137.
140
1912
138.
Further studies on the homogeneous hydrogenation of olefins using tris(triphenylphosphine)halogenorhodium(I) catalysts
Jardine F.H., Osbron J.A., Wilkinson G.
Journal of the Chemical Society A Inorganic Physical Theoretical , 1967
139.
Selective homogeneous hydrogenation of alk-1-enes using hydridocarbonyltris(triphenylphosphine)rhodium(I) as catalyst
O'Connor C., Wilkinson G.
Journal of the Chemical Society A Inorganic Physical Theoretical , 1968
140.
143
Friedl.
141.
On the Stability of Metallo‐Organic Compounds. II
Jaffé H.H.
Journal of Chemical Physics , 1954
142.
HYDROGENATION WITH COMPLEX METAL CATALYSTS
Lapporte S.J.
Annals of the New York Academy of Sciences , 1969
143.
Cyclooligomerisation von Butadien und Übergangsmetall‐π‐Komplexe
Wilke G., Arbeiten Bogdanovič N.B., Borner P., Breil H., Hardt P., Heimbach P., Herrmann G., Kaminsky H.-., Keim W., Kröner M., Müller H., Müller E.W., Oberkirch W., Schneider J., Stedefeder J., et. al.
Angewandte Chemie , 1963
144.
Katalysierte Synthese voncis-1,2-Divinylcyclobutan
Heimbach P., Brenner W.
Angewandte Chemie , 1967
145.
Allyl‐Übergangsmetall‐Systeme
Wilke G., Bogdanovic B., Hardt P., Heimbach P., Keim W., Kröner M., Oberkirch W., Tanaka K., Steinrücke E., Walter D., Zimmermann H.
Angewandte Chemie , 1966
146.
Molecular orbital studies of some transition metal complexes
Brouck�re G.
Theoretical Chemistry Accounts , 1970
147.
151
V. M. Rodionov
Zhur. Obshch. Khim. , 1936