Home / Articles / Haloalkenes activated by geminal groups in reactions with N-nucleophiles

Haloalkenes activated by geminal groups in reactions with N-nucleophiles

Alexander Yur'evich Rulev 1
Alexander Yur'evich Rulev
1 Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences
Published 30 November 1997
Communication , Volume 67, Issue 4, 279-293
29
Share
Cite this
GOST
 | 
Cite this
GOST
Rulev A. Y. Haloalkenes activated by geminal groups in reactions with N-nucleophiles // Russian Chemical Reviews. 1998. Vol. 67. No. 4. pp. 279-293.
GOST all authors (up to 50)
Rulev A. Y. Haloalkenes activated by geminal groups in reactions with N-nucleophiles // Russian Chemical Reviews. 1998. Vol. 67. No. 4. pp. 279-293.
RIS
 | 
Cite this
RIS
TY - JOUR
DO - 10.1070/RC1998v067n04ABEH000372
UR - https://rcr.colab.ws/publications/10.1070/RC1998v067n04ABEH000372
TI - Haloalkenes activated by geminal groups in reactions with N-nucleophiles
T2 - Russian Chemical Reviews
AU - Rulev, Alexander Yur'evich
PY - 1998
DA - 1997/11/30
PB - ANO Editorial Board of the journal Uspekhi Khimii
SP - 279-293
IS - 4
VL - 67
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors)
@article{1998_Rulev,
author = {Alexander Yur'evich Rulev},
title = {Haloalkenes activated by geminal groups in reactions with N-nucleophiles},
journal = {Russian Chemical Reviews},
year = {1998},
volume = {67},
publisher = {ANO Editorial Board of the journal Uspekhi Khimii},
month = {Nov},
url = {https://rcr.colab.ws/publications/10.1070/RC1998v067n04ABEH000372},
number = {4},
pages = {279--293},
doi = {10.1070/RC1998v067n04ABEH000372}
}
MLA
Cite this
MLA
Rulev, Alexander Yur'evich. “Haloalkenes activated by geminal groups in reactions with N-nucleophiles.” Russian Chemical Reviews, vol. 67, no. 4, Nov. 1998, pp. 279-293. https://rcr.colab.ws/publications/10.1070/RC1998v067n04ABEH000372.
Views / Visits / Downloads
16 / 16 / 3

Abstract

Reactions of nitrogen nucleophiles with haloalkenes in which the halogen atom occupies α-position with respect to an electron-withdrawing group are considered. Primary attention is devoted to the elucidation of the dependence of the reaction path on the nature of the nucleophile and substrate and on the reaction conditions. Possible mechanisms of nucleophilic substitution of vinylic halogen atoms in alkenes with activating and leaving groups attached to the same carbon atom are discussed. The bibliography includes 169 references.

References

1.
Domino Reactions in Organic Synthesis
Tietze L.F.
Chemical Reviews , 1996
2.
10.1021/cr950023+
3.
3
M. F. Shostakovskii
"Prostye Vinilovye Efiry" (Vinyl Ethers) , 1952
5.
5
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1953
6.
6
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1953
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
12.
13
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1954
13.
14
V. B. Evstigneev
Zhur. Fiz. Khim. , 1958
16.
17
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1958
17.
Purines, Pyrimidines, Pteridines, and Cancer
18.
β-Fur-yl-α-halogenacrylonitrile. II. Darstellung von β-Fur-2-yl-β(1,2,4-Triazolyl) Acrylonitrilen
Jähnisch K., Seeboth H., Krause E., Catasus N.
Journal für praktische Chemie , 1984
21.
22
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1958
23.
24
M. S. Ashkinazi
Dokl. Akad. Nauk SSSR , 1951
24.
2-Cyan-aziridin
Burzin K., Enderer K.
Angewandte Chemie , 1972
25.
Verbesserte Synthese von 2‐Cyan‐aziridinen und Untersuchungen zu ihrer Isomerisierung
Gundermann K., Burzin K., Sprenger F., Schulze H.
Chemische Berichte , 1972
29.
30
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1954
30.
β-Fur-2-yl-α-halogenacrylonitrile. VI. Darstellung von β-Fur-2-yl-β-aminoacrylonitrilen
Jähnisch K., Seeboth H., Weigt A., Callejas D.R., Catasus N.
Journal für praktische Chemie , 1987
31.
Unconventional nucleotide analogues—II
Nollet A.J., Pandit U.K.
Tetrahedron , 1969
32.
33
M. B. Neiman
"Issledovanie Mekhanizma Okisleniya Butana" (Research on the Mechanism of the Oxidation of Butane) , 1939
33.
34
G. W. Robinson
J. Chem. Phys. , 1886
34.
Pseudoesters and Derivatives. XVIII. The Reaction of 5-Methoxyfuran-2(5H)-one and Its 3-Halo Derivatives with Nitrogen and Sulphur Nucleophiles
35.
36
J. Billon
Bull. Soc. chim. France , 1960
37.
38
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1956
38.
39
V. F. Gachkovskii
Biofizika , 1959
39.
40
A. A. Krasnovskii
Biofizika , 1960
40.
41
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1950
41.
42
L. K. Obukhova
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk , 1960
43.
44
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1953
44.
45
W. Hendrich
Roczniki Chemii , 1958
46.
Facile construction of terpenoid frameworks by cycloadditions with methyl 2-chlorocyclopropylidenacetate
Spitzner D., Engler A., Wagner P., De Meijere A., Bengtson G., Simon A., Peters K., Peters E.
Tetrahedron , 1987
51.
Azapenams: An Efficient Approach to a Novel Class of β-Lactams1
Es-Sayed M., Heiner T., de Meijere A.
Synlett , 1993
54.
New short syntheses of isoquinoline-4-carboxylic acid and 2-aza-3,3a-dihydroazulene-3a-carboxylic acid derivatives
Wessjohann L., Skattebøl L., De Meijere A.
Journal of the Chemical Society Chemical Communications , 1990
58.
59
H. Linshitz
"Research in Photosynthesis" , 1957
60.
61
A. N. Terenin
1959
61.
62
A. A. Krasnovskii
"Sbornik, Voprosy Khimicheskoi Kinetiki" (Symposium, Problems of Chemical Kinetics) , 1955
62.
63
1930
63.
64
Chem. Zentr. II , 1931
64.
Reaction of some coumarin and 4,6-diaryl-2H-pyran derivatives with secondary amines
El-Kholy I.E., Mishrikey M.M., Feid-Allah H.M.
Journal of Heterocyclic Chemistry , 1981
65.
66
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1950
67.
A Novel Synthesis of 4-Aminomethylcoumarins
Kelkar R.M., Joshi U.K., Paradkar M.V.
Synthesis , 1986
68.
69
B. Commoner
1958
69.
70
N. Bubnov
Biofizika , 1960
70.
3-Amino-chromanole-(4) als potentielle Sympathomimetika
auf dem Keller H.H., Zymalkowski F.
Archiv der Pharmazie , 1971
71.
72
A. F. Lukovnikov
"Starenie i Stabilizatsiya Polimerov" (Aging arid Stabilisation of Polymers) , 1963
72.
Imidazolyl derivatives of the chroman ring. 2
Cozzi P., Pillan A.
Journal of Heterocyclic Chemistry , 1985
73.
Imidazolyl derivatives of the thiochroman ring
Cozzi P., Pillan A.
Journal of Heterocyclic Chemistry , 1988
74.
75
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1950
75.
76
A. N. Terenin
"Fotokhimiya Krasitelei" (The Photochemistry of Dyes) , 1947
76.
A Novel Rearrangement of Ethylenimine Ketones
Pohland A.E., McMaster M.C., Badger R.C., Cromwell N.H.
Journal of the American Chemical Society , 1965
78.
Regio- and Stereoselective Synthesis of Steroidal Amines
Koga T., Nogami Y., Yamanaka S.
Synthesis , 1986
80.
81
J. C. Ghosh
J. Indian Chem. Soc. , 1934
81.
82
G. P. Brin
Biokhimiya , 1957
82.
Reaction of 6-bromobenzocyclohepten-5-one with amines
Iriarte J., Camargo C., Crabbé P.
Journal of the Chemical Society Perkin Transactions 1 , 1980
83.
84
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1947
84.
85
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1947
86.
The role of solvent in conjugate additions leading tocisandtrans-1-Alkyl-2-aryl-3-carbo(aroyl)aziridines
Tarburton P., Woller P.B., Badger R.C., Doomes E., Cromwell N.H.
Journal of Heterocyclic Chemistry , 1977
87.
The synthesis and spectra of new (E)-(trans) and (Z)-(cis)-1-alkyl-2-aryl (alkyl) - 3 -aroylaziridines
Tarburton P., Wolpa L.J., Loerch R.K., Folsom T.L., Cromwell N.H.
Journal of Heterocyclic Chemistry , 1977
88.
89
A. A. Krasnovskii
Izd. Akad. Nauk SSSR, Moscow , 1955
89.
90
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1951
90.
Synthése, stéréochimie, et réactivité thermique de (N-méthylidenealkylamino)-2 aziridines
Gelas-Mialhe Y., Hierle R., Vessière R.
Journal of Heterocyclic Chemistry , 1974
91.
Condensation products of 2-bromo-3-substituted-inden-1-ones with several primary amines
Nan'ya S., Kitahara T., Fujii K., Bajji A.C., Butsugan Y.
Journal of Heterocyclic Chemistry , 1992
92.
93
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1956
94.
95
A. A. Krasnovskii
Fiziologiya Rastenii , 1957
95.
A New Synthetic Route to 2-Dialkylamino-2-alkenals
Keiko N.A., Rulev A.Y., Kalikhman I.D., Voronkov M.G.
Synthesis , 1989
96.
97
A. N. Terenin
Dokl. Akad. Nauk SSSR , 1952
97.
98
W. Franke
Chem. Zentr. , 1954
98.
99
V. V. Zolotarev
1938
99.
100
V. V. Zolotarev
Chem. Abs. , 1941
100.
101
M. F. Shostakovskii
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk , 1960
101.
102
F. Fichter
Helv. Chim. Acta , 1922
103.
New Synthesis of Uric Acid and 1,7-Dimethyluric Acid1
Bills C.W., Gebura S.E., Meek J.S., Sweeting O.J.
Journal of Organic Chemistry , 1962
104.
105
F. F. Litvin
Dokl. Akad. Nauk SSSR , 1958
106.
New One-Step Synthesis of Functionalized 2-Imidazolines
Marsura A., Luu-Duc C., Gellon G.
Synthesis , 1985
107.
108
F. Fichter
Helv. Chim. Acta , 1924
108.
109
F. Ficher
Bull. Soc. chim. France (4) , 1916
109.
C-nucleosides aminoisoxazoliques. Communication préliminaire
Tronchet J.M., Martin O.R., Grouiller A., Sarda N.
Helvetica Chimica Acta , 1979
111.
β-Fur-2-yl-α-halogen-acrylonitrile; Darstellung von 3-Amino-5-für-2-yl-isoxazolen
112.
113
H. Blum
"Photodynamic Action and Diseases caused Light" , 1940
113.
Eidem Å., Undheim K., Reistad K.R., Sjöstrand E., Lagerlund I., Ehrenberg L.
Acta Chemica Scandinavica , 1971
114.
Undheim K., Lie R., Johanson R., Hytta R., van der Hoeven M.G., Swahn C.
Acta Chemica Scandinavica , 1973
115.
The chemistry of 4-mercaptoazetidin-2-ones. Part 2. Synthesis of bisnorpenicillins
Osborne N.F.
Journal of the Chemical Society Perkin Transactions 1 , 1980
118.
Synthesis of indeno[2,1-b][1,4]benzothiazine derivatives from 2-bromoinden-1-ones
Bajji A.C., Nan'ya S., Butsugan Y.
Journal of Heterocyclic Chemistry , 1993
119.
Condensations of brominated products ofo-acetylbenzophenone with several primary amines
Nan'Ya S., Ishida H., Moiji E.J., Butsugan Y., Bajji A.C.
Journal of Heterocyclic Chemistry , 1994
120.
Efficient Olefin Synthesis Using the Pyrazinylsulfunyl Group
Nozoe H., Ohta A., Tonomura Y., Odashima H., Fujiwara N., Shimazaki M.
Heterocycles , 1989
122.
123
V. V. Levchenko
Zhur. Obshch. Khim. , 1952
123.
124
V. V. Levchenko
Zhur. Obshch. Khim. , 1952
124.
β-Ketovinylation
Rybinskaya M.I., Nesmeyanov A.N., Kochetkov N.K.
Russian Chemical Reviews , 1969
125.
127
R. Pasternak
Helv. Chim. Acta , 1948
126.
128
J. Wiemann
Bull. Soc. chim. France , 1952
127.
129
J. Wiemann
Bull. Soc. chim. France , 1955
128.
130
J. Wiemann
Bull. Soc. chim. France , 1958
130.
132
G. Shima
Kyoto Univ. , 1929
133.
Regioselectivite des substitutions nucleophiles sur des fluoro olefines fonctionnelles
Nguyen T., Rubinstein M., Wakselman C.
Journal of Fluorine Chemistry , 1978
134.
Darstellung und Umsetzungen von perhalogenierten α.β‐ungesättigten Ketonen
135.
137
S. R. Rafikov
Zh. Obshch. Khim. , 1944
136.
138
S. Ono
J. Chem. Soc. Japan , 1957
137.
139
I. L. Knunyants
1959
138.
140
1912
139.
New pyridazinones: synthesis and correlation between structure and α-blocking activity
Corsano S., Scapicchi R., Strappaghetti G., Marucci G., Paparelli F.
European Journal of Medicinal Chemistry , 1993
145.
A facile synthesis of staurosporine aglycone
Xie G., William Lown J.
Tetrahedron Letters , 1994
146.
Darstellung von 1,3-Bis(3,4-dihalogen-5-oxo-furan-2-yl)-harnstoff
Jähnisch K., Seeboth H., Pinon D.
Zeitschrift für Chemie , 2010
148.
Pyrimidine derivatives.VII. Nucleophilic reactions of 5-bromo-1-(bromoalkyl)-6-bromomethyl-2,4(1H,3H)-pyrimidinediones
Kinoshita T., Takaishi Y., Okunaka T., Ohwada T., Furukawa S.
Journal of Heterocyclic Chemistry , 1992
149.
A Mild And Efficient Synthesis of Diamino-Steroids
Koga T., Nogami Y., Toh N., Nishimura K.
Synthetic Communications , 1986
150.
152
W. Albert
Trans. Electrochem. Soc. , 1943
151.
153
1899
152.
154
Friedl.
153.
155
M. V. Mal'tsev
Izv. Vys. Ucheb. Zaved., Tsvet. Met. , 1960
154.
156
J. S. Fruton
J. Biol. Med. , 1950
155.
157
1903
156.
158
Friedl.
157.
159
J. Tafel
Z. Elektrochem. , 1911
158.
160
1912
159.
Reactions of 3-bromo-2,3-dihydro- and 2,3-dibromo-4H-1-benzothiopyran-4-one 1,1-dioxides with various amines
Watanabe S., Nakazumi H., Kitao T.
Journal of the Chemical Society Perkin Transactions 1 , 1988
160.
Synthesis and absorption spectra of 2-substituted 5,8-dimethoxy-4H-1-benzothiopyran-4-one 1,1-dioxides
Watanabe S., Nakazumi H., Akagi N., Maeda K., Kitao T.
Journal of Heterocyclic Chemistry , 1990
162.
The rich mechanistic world of nucleophilic vinylic (SN V) substitution
Rappoport Z.
Recueil des Travaux Chimiques des Pays-Bas , 1985
163.
α-Chloro-β-amino Ketones
Cromwell N.H., Wankel R.A.
Journal of the American Chemical Society , 1948
164.
The Stereoisomeric α,β-Dimorpholinyl-Benzylacetophenones
Jordan R.H., Lutz R.E., Hinkley D.F.
Journal of Organic Chemistry , 1951
165.
The Reaction Mechanism of α-Bromo-α, β-unsaturated Ketones with Amines
Inokawa H.
Bulletin of the Chemical Society of Japan , 1964
166.
Small Charged Rings. VIII. Isolation and Stereochemistry of Acyl Aziridinium Salt Intermediates1,2
167.
169
Friedl.
168.
170
1918
169.
171
Friedl.
171.
173
Friedl.
172.
174
S. Calvert
India Rubber Tire Rev. , 1926
173.
Synthesis of β,γ-Unsaturated Esters from α,β-Unsaturated Acid Chlorides
Cardillo G., De Simone A., Mingardi A., Tomasini C.
Synlett , 1995
174.
176
G. V. Samsonov
"Metody Ispytaniya na Mikrotverdost' i Pribory" (Methods of Microhardness Testing and Apparatus) , 1965