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.
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
7.
Cromwell N.H.
Chemical Reviews ,
1946
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.
Shainyan B.A.
Russian Chemical Reviews ,
1986
11.
Suminov S.I., Kost A.N.
Russian Chemical Reviews ,
1969
12.
13
V. B. Evstigneev
Dokl. Akad. Nauk SSSR ,
1954
13.
14
V. B. Evstigneev
Zhur. Fiz. Khim. ,
1958
14.
Gundermann K., Holtmann G.
Chemische Berichte ,
1958
15.
Wessjohann L., Mcgaffin G., de Meijere A.
Synthesis ,
1989
16.
17
V. B. Evstigneev
Dokl. Akad. Nauk SSSR ,
1958
17.
A. Montgomery J.
Heterocycles ,
1984
18.
Jähnisch K., Seeboth H., Krause E., Catasus N.
Journal für praktische Chemie ,
1984
19.
Tronchet J.M., Martin O.R.
Helvetica Chimica Acta ,
1977
20.
Jähnisch K., Seeboth H., Krause E., Callejas D.R.
Journal für praktische Chemie ,
1984
21.
22
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1958
22.
Jähnisch K., Gründemann E.
Journal für praktische Chemie ,
1986
23.
24
M. S. Ashkinazi
Dokl. Akad. Nauk SSSR ,
1951
24.
25.
Gundermann K., Burzin K., Sprenger F., Schulze H.
Chemische Berichte ,
1972
26.
Tronchet J.M., Martin O.R.
Helvetica Chimica Acta ,
1976
27.
Tronchet J.M., Martin O.R.
Carbohydrate Research ,
1981
28.
Wagner-Jauregg T.
Helvetica Chimica Acta ,
1961
29.
30
V. B. Evstigneev
Dokl. Akad. Nauk SSSR ,
1954
30.
Jähnisch K., Seeboth H., Weigt A., Callejas D.R., Catasus N.
Journal für praktische Chemie ,
1987
31.
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.
Fariña F., Victoria Mart地 M., S�chez F., Carmen Maestro M., Rosario Mart地 M.
Heterocycles ,
1983
35.
36
J. Billon
Bull. Soc. chim. France ,
1960
36.
Lown J.W., Itoh T., Ono N.
Canadian Journal of Chemistry ,
1973
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
42.
Harada K., Nakamura I.
Heterocycles ,
1978
43.
44
V. B. Evstigneev
Dokl. Akad. Nauk SSSR ,
1953
44.
45
W. Hendrich
Roczniki Chemii ,
1958
45.
46.
Spitzner D., Engler A., Wagner P., De Meijere A., Bengtson G., Simon A., Peters K., Peters E.
Tetrahedron ,
1987
47.
Seyed-Mahdavi F., Teichmann S., de Meijere A.
Tetrahedron Letters ,
1986
48.
Wessjohann L., Krass N., Yu D., Meijere A.D.
Chemische Berichte ,
1992
49.
Krass N., Wessjohann L., Yu D., Meijere A.
1989
50.
Giller K., Baird M.S., de Meijere A.
Synlett ,
1992
51.
Es-Sayed M., Heiner T., de Meijere A.
Synlett ,
1993
52.
Liese T., Teichmann S., de Meijere A.
Synthesis ,
1988
53.
de Meijere A., Wessjohann L.
Synlett ,
1990
54.
Wessjohann L., Skattebøl L., De Meijere A.
Journal of the Chemical Society Chemical Communications ,
1990
55.
Wessjohann L., Giller K., Zuck B., Skatteboel L., de Meijere A.
Journal of Organic Chemistry ,
1993
56.
Es-Sayed M., Gratkowski C., Krass N., Meyers A.I., de Meijere A.
Synlett ,
1992
57.
Es-Sayed M., Gratkowski C., Krass N., Meyers A.I., de Meijere A.
Tetrahedron Letters ,
1993
58.
59
H. Linshitz
"Research in Photosynthesis" ,
1957
59.
Oh C., Yi I., Park K.P.
Journal of Heterocyclic Chemistry ,
1994
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.
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
66.
Nakazumi H., Kobara Y., Kitao T.
Journal of Heterocyclic Chemistry ,
1992
67.
Kelkar R.M., Joshi U.K., Paradkar M.V.
Synthesis ,
1986
68.
69
B. Commoner
1958
69.
70
N. Bubnov
Biofizika ,
1960
70.
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.
Cozzi P., Pillan A.
Journal of Heterocyclic Chemistry ,
1985
73.
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.
Pohland A.E., McMaster M.C., Badger R.C., Cromwell N.H.
Journal of the American Chemical Society ,
1965
77.
Cromwell N.H., McMaster M.C.
Journal of Organic Chemistry ,
1967
78.
Koga T., Nogami Y., Yamanaka S.
Synthesis ,
1986
79.
Koga T., Nogami Y., Toh N., Nishimura K.
Synthetic Communications ,
1983
80.
81
J. C. Ghosh
J. Indian Chem. Soc. ,
1934
81.
82
G. P. Brin
Biokhimiya ,
1957
82.
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
85.
Gammill R.B., Nash S.A., Mizsak S.A.
Tetrahedron Letters ,
1983
86.
Tarburton P., Woller P.B., Badger R.C., Doomes E., Cromwell N.H.
Journal of Heterocyclic Chemistry ,
1977
87.
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.
Gelas-Mialhe Y., Hierle R., Vessière R.
Journal of Heterocyclic Chemistry ,
1974
91.
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
93.
My Thu Truong-Nguyen T., Togo H., Schlosser M.
Tetrahedron ,
1994
94.
95
A. A. Krasnovskii
Fiziologiya Rastenii ,
1957
95.
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
102.
Jähnisch K., Seeboth H., Kuban R.J.
Journal für praktische Chemie ,
1987
103.
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
105.
Marsura A., Luu Duc C.
Synthesis ,
1982
106.
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.
Tronchet J.M., Martin O.R., Grouiller A., Sarda N.
Helvetica Chimica Acta ,
1979
110.
Tronchet J.M., Martin O., Zumwald J., Le-Hong N., Perret F.
Helvetica Chimica Acta ,
1975
111.
Jöhnisch K., Seeboth H., Catasus N.
Zeitschrift für Chemie ,
2010
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.
Osborne N.F.
Journal of the Chemical Society Perkin Transactions 1 ,
1980
116.
Osborne N.F.
Journal of the Chemical Society Perkin Transactions 1 ,
1980
117.
Greengrass C.W., Hoople D.W., Nobbs M.S.
Tetrahedron Letters ,
1982
118.
Bajji A.C., Nan'ya S., Butsugan Y.
Journal of Heterocyclic Chemistry ,
1993
119.
Nan'Ya S., Ishida H., Moiji E.J., Butsugan Y., Bajji A.C.
Journal of Heterocyclic Chemistry ,
1994
120.
Nozoe H., Ohta A., Tonomura Y., Odashima H., Fujiwara N., Shimazaki M.
Heterocycles ,
1989
121.
Nitta M., Mori S., Iino Y.
Heterocycles ,
1991
122.
123
V. V. Levchenko
Zhur. Obshch. Khim. ,
1952
123.
124
V. V. Levchenko
Zhur. Obshch. Khim. ,
1952
124.
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
129.
QingHua Chen, Zhe Geng, Bin Huang
Tetrahedron Asymmetry ,
1995
130.
132
G. Shima
Kyoto Univ. ,
1929
131.
Dondy B., Doussot P., Portella C.
Tetrahedron Letters ,
1994
132.
Dondy B., Doussot P., Iznaden M., Muzard M., Portella C.
Tetrahedron Letters ,
1994
133.
Nguyen T., Rubinstein M., Wakselman C.
Journal of Fluorine Chemistry ,
1978
134.
Scherer O., Hörlein G., Millauer H.
Chemische Berichte ,
1966
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.
Corsano S., Scapicchi R., Strappaghetti G., Marucci G., Paparelli F.
European Journal of Medicinal Chemistry ,
1993
140.
Varga I., Jerkovich G., Màtyus P.
Journal of Heterocyclic Chemistry ,
1991
141.
M�yus P., Z�a-Kaczi� E.
Heterocycles ,
1993
142.
Totani R., Sako M., Hirota K., Maki Y.
Journal of the Chemical Society Perkin Transactions 1 ,
1994
143.
Sugimoto T., Matsuura S.
Bulletin of the Chemical Society of Japan ,
1980
144.
Pfleiderer W., Deiss H.
Chemische Berichte ,
1971
145.
Xie G., William Lown J.
Tetrahedron Letters ,
1994
146.
Jähnisch K., Seeboth H., Pinon D.
Zeitschrift für Chemie ,
2010
147.
KINOSHITA T., NAKAHATA N., KOUCHI A., FURUKAW S.
Chemical and Pharmaceutical Bulletin ,
2011
148.
Kinoshita T., Takaishi Y., Okunaka T., Ohwada T., Furukawa S.
Journal of Heterocyclic Chemistry ,
1992
149.
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.
Watanabe S., Nakazumi H., Kitao T.
Journal of the Chemical Society Perkin Transactions 1 ,
1988
160.
Watanabe S., Nakazumi H., Akagi N., Maeda K., Kitao T.
Journal of Heterocyclic Chemistry ,
1990
161.
162.
Rappoport Z.
Recueil des Travaux Chimiques des Pays-Bas ,
1985
163.
Cromwell N.H., Wankel R.A.
Journal of the American Chemical Society ,
1948
164.
Jordan R.H., Lutz R.E., Hinkley D.F.
Journal of Organic Chemistry ,
1951
165.
Inokawa H.
Bulletin of the Chemical Society of Japan ,
1964
166.
Leonard N.J., Ning R.Y., Booth R.L.
Journal of Organic Chemistry ,
1965
167.
169
Friedl.
168.
170
1918
169.
171
Friedl.
170.
Kauffman T., Risberg A., Schulz J., Weber R.
Tetrahedron Letters ,
1964
171.
173
Friedl.
172.
174
S. Calvert
India Rubber Tire Rev. ,
1926
173.
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