Abstract
A systematic account is given of data on the reactions of cyclopropene derivatives with acids, halogen- and sulfur-containing electrophiles, and mercury salts. The influence of the nature of the electrophile and of the structure of cyclopropene on processes with retention and opening of the ring, on the stereochemistry of the addition of reactants to the cyclopropene bond, and on the stereochemistry of the formation of the ring opening products is examined. The reaction mechanisms are discussed. The bibliography includes 120 references.
References
1.
1
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1948
2.
2
A. A. Krasnovskii
Zhur. Fiz. Khim. ,
1956
3.
4.
4
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1949
5.
Zefirov N.S., Sokolov V.I.
Russian Chemical Reviews ,
1967
6.
Kozina M.P., Mastryukov V.S., Mil'vitskaya E.M.
Russian Chemical Reviews ,
1982
7.
Kolesov V.P., Kozina M.P.
Russian Chemical Reviews ,
1986
8.
Dill J.D., Greenberg A., Liebman J.F.
Journal of the American Chemical Society ,
1979
9.
Lien M.H., Hopkinson A.C.
Journal of Molecular Structure THEOCHEM ,
1987
10.
Wiberg K.B., Artis D.R., Bonneville G.
Journal of the American Chemical Society ,
1991
11.
Billups W.E., Lee G.A., Arney B.E., Whitmire K.H.
Journal of the American Chemical Society ,
1991
12.
Padwa A., Wannamaker M.W.
Tetrahedron ,
1991
13.
15
A. S. Holt
"Research in Photosynthesis" ,
1957
14.
16
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1949
15.
17
V. B. Evstigneev
Dokl. Akad. Nauk SSSR ,
1958
16.
18
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1951
17.
Aue D.H., Helwig G.S.
Tetrahedron Letters ,
1974
18.
20
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1954
19.
21
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1958
20.
22
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1958
21.
23
N. V. Vostrilova
Dokl. Akad. Nauk Uzbek. SSR ,
1958
22.
24
M. S. Ashkinazi
Dokl. Akad. Nauk SSSR ,
1951
23.
Padwa A., Rieker W.F.
Journal of the American Chemical Society ,
1981
24.
26
B. Ya. Dain
1957
25.
Skancke A.
Journal of Molecular Structure ,
1976
26.
Kao J., Radom L.
Journal of the American Chemical Society ,
1978
27.
Allen F.H.
Tetrahedron ,
1982
28.
Protopopova M.N., Shapiro E.A.
Russian Chemical Reviews ,
1989
29.
32
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1952
30.
33
M. B. Neiman
"Issledovanie Mekhanizma Okisleniya Butana" (Research on the Mechanism of the Oxidation of Butane) ,
1939
31.
Schmitz E., Sonnenschein H., Kuban R.J.
Tetrahedron Letters ,
1985
32.
Padwa A., Kennedy G.D.
Journal of Organic Chemistry ,
1984
33.
36
J. Billon
Bull. Soc. chim. France ,
1960
34.
Komendantov M.I., Bekmukhametov R.R., Domnin I.N.
Tetrahedron ,
1978
35.
38
V. B. Evstigneev
Dokl. Akad. Nauk SSSR ,
1956
36.
Galle J.E., Hassner A.
Journal of the American Chemical Society ,
1972
37.
Binger P., Schäfer H.
Tetrahedron Letters ,
1975
38.
Mikhailov B.M., Bubnov Y.N., Nesmeyanova O.A., Kiselev V.G., Rudashevskaya T.Y., Kazansky B.A.
Tetrahedron Letters ,
1972
39.
42
L. K. Obukhova
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk ,
1960
40.
43
N. Bunge
Ber. Deutsch. Chem. Ges. ,
1870
41.
Padwa A., Blacklock T.J., Loza R.
Journal of the American Chemical Society ,
1981
42.
Bee L.K., Garratt P.J., Mansuri M.M.
Journal of the American Chemical Society ,
1980
43.
Billups W.E., Chamberlain W.T., Asim M.Y.
Tetrahedron Letters ,
1977
44.
47
G. Oster
"Research in Photosynthesis" ,
1957
45.
Friedrich L.E., Cormier R.A.
Journal of Organic Chemistry ,
1970
46.
Friedrich L.E., Cormier R.A.
Tetrahedron Letters ,
1971
47.
Crandall J.K., Conover W.W.
Journal of Organic Chemistry ,
1978
48.
Maynard G.D., Paquette L.A.
Journal of Organic Chemistry ,
1991
49.
Wiberg K.B., Bartley W.J.
Journal of the American Chemical Society ,
1960
50.
53
D. Porretand E. Rabinowitch
Nature ,
1937
51.
54
R. Livingston
J. Phys. Chem. ,
1941
52.
55
G. A. Bogdanovskii
1958
53.
56
T. Iasui
Bull. Chem. Soc. Japan. ,
1935
54.
57
R. Livingston
"Research in Photosynthesis" ,
1957
55.
58
N. E. Khomutov
1953
56.
59
H. Linshitz
"Research in Photosynthesis" ,
1957
57.
60
A. N. Terenin
Optika i Spektrosk. ,
1956
58.
61
A. N. Terenin
1959
59.
Vincens M., Choubani S., Vidal M.
Tetrahedron Letters ,
1981
60.
63
1930
61.
Birchall J.M., Burger K., Haszeldine R.N., Nona S.N.
Journal of the Chemical Society Perkin Transactions 1 ,
1981
62.
63.
Rasteikiene L., Greiciute D., Lin'kova M.G., Knunyants I.L.
Russian Chemical Reviews ,
1977
64.
68
N. N. Mel'nikov
Zhur. Obshch. Khim. ,
1946
65.
Smit V.A., Zefirov N.S., Bodrikov I.V., Krimer M.Z.
Accounts of Chemical Research ,
1979
66.
Smith J.A., Brintzinger H.H.
Journal of Organometallic Chemistry ,
1981
67.
71
Yu. A. Shlyapnikov
Vysokomol. Soed. ,
1962
68.
72
A. F. Lukovnikov
"Starenie i Stabilizatsiya Polimerov" (Aging arid Stabilisation of Polymers) ,
1963
69.
Kartashev V.R., Bodrikov I.V., Skorobogatova E.V., Zefirov N.S.
Phosphorous and Sulfur and the Related Elements ,
1977
70.
Kartashov V.R., Skorobogatova E.V., Grudzinskaja E.Y., Akimkina N.F., Zefirov N.S., Caple R.
Tetrahedron ,
1985
71.
Zefirov N.S., Koz'min A.S., Zhdakin V.V.
Tetrahedron ,
1982
72.
Zefirov N.S., Koz'min A.S., Kirin V.N., Zhdankin V.V., Caple R.
Journal of Organic Chemistry ,
1981
73.
77
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1948
74.
78
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1949
75.
79
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1952
76.
80
N. N. Mel'nikov
Zhur. Obshch. Khim. ,
1937
77.
81
J. C. Ghosh
J. Indian Chem. Soc. ,
1934
78.
82
G. P. Brin
Biokhimiya ,
1957
79.
83
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1947
80.
84
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1947
81.
85
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1947
82.
Fahey R.C.
Topics in Stereochemistry ,
1968
83.
Traylor T.G.
Accounts of Chemical Research ,
1969
84.
Bach R.D., Richter R.F.
Journal of the American Chemical Society ,
1972
85.
89
A. A. Krasnovskii
Izd. Akad. Nauk SSSR, Moscow ,
1955
86.
90
V. B. Evstigneev
Dokl. Akad. Nauk SSSR ,
1951
87.
88.
Shirafuji T., Yamamoto Y., Nozaki H.
Tetrahedron Letters ,
1971
89.
Shirafuji T., Nozaki H.
Tetrahedron ,
1973
90.
94
A. A. Krasnovskii
Fiziologiya Rastenii ,
1957
91.
95
A. A. Krasnovskii
Fiziologiya Rastenii ,
1957
92.
96
L. M. Vorob'eva
Biokhimiya ,
1958
93.
97
A. N. Terenin
Dokl. Akad. Nauk SSSR ,
1952
94.
98
W. Franke
Chem. Zentr. ,
1954
95.
99
V. V. Zolotarev
1938
96.
100
V. V. Zolotarev
Chem. Abs. ,
1941
97.
101
M. F. Shostakovskii
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk ,
1960
98.
102
F. Fichter
Helv. Chim. Acta ,
1922
99.
103
L. N. Bell
Dokl. Akad. Nauk SSSR ,
1956
100.
104
O. P. Osipova
Dokl. Akad. Nauk SSSR ,
1950
101.
Zefirov N.S., Gurvich L.G.
Journal of Organometallic Chemistry ,
1974
102.
Klein J., Levene R.
Tetrahedron Letters ,
1969
103.
Chamberlain P., Whitham G.H.
Journal of the Chemical Society B Physical Organic ,
1970
104.
108
F. Fichter
Helv. Chim. Acta ,
1924
105.
109
F. Ficher
Bull. Soc. chim. France (4) ,
1916
106.
110
M. F. Shostakovskii
Dokl. Akad. Nauk SSSR ,
1960
107.
111
M. Calvin
1956
108.
112
A. G. Pozdeeva
Zhur. Prikl. Khim. ,
1952
109.
113
H. Blum
"Photodynamic Action and Diseases caused Light" ,
1940
110.
Dewar M.J., Ford G.P.
Journal of the American Chemical Society ,
1979
111.
115
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1957
112.
116
V. B. Evstigneev
Dokl. Akad. Nauk SSSR ,
1957
113.
117
V. V. Levchenko
Zhur. Obshch. Khim. ,
1948
114.
Yamabe S., Minato T., Inagaki S.
Journal of the Chemical Society Chemical Communications ,
1988
115.
Hase H., Müller C., Schweig A.
Tetrahedron ,
1978
116.
Lien M.H., Hopkinson A.C.
Journal of Molecular Structure THEOCHEM ,
1985
117.
Meyer H., Schmidt-Lukasch G., Baum G., Massa W., Berndt A.
Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences ,
1988
118.
122
S. R. Rafikov
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk ,
1953
119.
123
V. V. Levchenko
Zhur. Obshch. Khim. ,
1952
120.
124
V. V. Levchenko
Zhur. Obshch. Khim. ,
1952
121.
Radom L., Hariharan P.C., Pople J.A., Schleyer P.V.
Journal of the American Chemical Society ,
1973
122.
Clark D.T., Smale G.
Tetrahedron ,
1969
123.
Jensen A.
Theoretical Chemistry Accounts ,
1983
124.
Aksenov V.S., Terent'eva G.A., Savinykh Y.V.
Russian Chemical Reviews ,
1980