Abstract
Traditional and new procedures for epoxidation of substituted norbornenes are described. The stereochemistry of this reaction and the influence of substituents on the reactivity of the substrate are analysed. The molecular rearrangements and heterocyclisation reactions that can accompany epoxidation are considered; examples of selective attack of oxidants at one of the double bonds in norbornenes containing an unsaturated substituent and also at a multiple bond in some polycyclic di- and triene systems are given. The bibliography includes 252 references.
References
1.
1
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1948
2.
2
A. A. Krasnovskii
Zhur. Fiz. Khim. ,
1956
3.
Filippova T.V., Blyumberg E.A.
Russian Chemical Reviews ,
1982
4.
Berti G.
Topics in Stereochemistry ,
1973
5.
Dryuk V.G.
Russian Chemical Reviews ,
1985
6.
Lazurin E.A., Voronenkov V.V., Osokin Y.G.
Russian Chemical Reviews ,
1977
7.
Gorman A.A., Rodgers M.A.
Chemical Society Reviews ,
1981
8.
9.
12
V. B. Evstigneev
Dokl. Akad. Nauk SSSR ,
1950
10.
13
V. B. Evstigneev
Dokl. Akad. Nauk SSSR ,
1954
11.
14
V. B. Evstigneev
Zhur. Fiz. Khim. ,
1958
12.
Kwart H., Vosburgh W.G.
Journal of the American Chemical Society ,
1954
13.
Walborsky H.M., Loncrini D.F.
Journal of the American Chemical Society ,
1954
14.
17
V. B. Evstigneev
Dokl. Akad. Nauk SSSR ,
1958
15.
Azman A., Borstnik B., Plesnicar B.
Journal of Organic Chemistry ,
1969
16.
Plesnicar B., Tasevski M., Azman A.
Journal of the American Chemical Society ,
1978
17.
Lynch B.M., Pausacker K.H.
Journal of the Chemical Society (Resumed) ,
1955
18.
21
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1958
19.
22
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1958
20.
Zefirov N.S., Sokolov V.I.
Russian Chemical Reviews ,
1967
21.
24
M. S. Ashkinazi
Dokl. Akad. Nauk SSSR ,
1951
22.
25
G. W. Robinson
J. Chem. Phys. ,
1955
23.
24.
27
A. A. Krasnovskii
Biofizika ,
1956
25.
28
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1955
26.
29
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1951
27.
30
V. B. Evstigneev
Dokl. Akad. Nauk SSSR ,
1954
28.
31
A. A. Krasnovskii
Biokhimiya ,
1960
29.
Claret F., Carrupt P., Vogel P.
Helvetica Chimica Acta ,
1987
30.
31.
34
G. W. Robinson
J. Chem. Phys. ,
1886
32.
Koola J.D., Kochi J.K.
Journal of Organic Chemistry ,
1987
33.
36
J. Billon
Bull. Soc. chim. France ,
1960
34.
Hutter R., Mallat T., Baiker A.
Journal of Catalysis ,
1995
35.
Arias L.A., Adkins S., Nagel C.J., Bach R.D.
Journal of Organic Chemistry ,
1983
36.
Osei-Twum E.Y., Warkentin J.
Journal of Organic Chemistry ,
1985
37.
Tezuka T., Iwaki M.
Journal of the Chemical Society Perkin Transactions 1 ,
1984
38.
Bloch R., Abecassis J., Hassan D.
Journal of Organic Chemistry ,
1985
39.
Kim Y.H., Chung B.C.
Journal of Organic Chemistry ,
1983
40.
Murray R.W., Jeyaraman R.
Journal of Organic Chemistry ,
1985
41.
44
V. B. Evstigneev
Dokl. Akad. Nauk SSSR ,
1953
42.
45
W. Hendrich
Roczniki Chemii ,
1958
43.
Bartlett P.D., Banavali R.
Journal of Organic Chemistry ,
1991
44.
Duschek C., Grimm W., Hampel M., Jauch R., Pritzkow W., Rosner R.
Journal für praktische Chemie ,
1975
45.
48
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1955
46.
49
A. A. Krasnovskii
Biofizika ,
1958
47.
Roberts J.T., Madix R.J.
Journal of the American Chemical Society ,
1988
48.
Cant N.W., Kennedy E.M., Ossipoff N.J.
Catalysis Letters ,
1991
49.
Corma A., Navarro M.T., Pariente J.P.
Journal of the Chemical Society Chemical Communications ,
1994
50.
Adam W., Pasquato L.
Tetrahedron Letters ,
1987
51.
Sasaki T.
Journal of the American Chemical Society ,
1981
52.
55
G. A. Bogdanovskii
1958
53.
Jefford C.W., Boschung A.F.
Helvetica Chimica Acta ,
1974
54.
Jefford C.W., Boschung A.F., Rimbault C.G.
Helvetica Chimica Acta ,
1976
55.
58
N. E. Khomutov
1953
56.
59
H. Linshitz
"Research in Photosynthesis" ,
1957
57.
Andrews M.A., Cheng C.W.
Journal of the American Chemical Society ,
1982
58.
Chauvet F., Heumann A., Waegell B.
Tetrahedron Letters ,
1984
59.
Chauvet F., Heumann A., Waegell B.
Journal of Organic Chemistry ,
1987
60.
63
1930
61.
Vach H.
Chemical Physics Letters ,
1990
62.
65
A. A. Krasnovskii
Biofizika ,
1959
63.
Yamada T., Takai T., Rhode O., Mukaiyama T.
Chemistry Letters ,
1991
64.
Saalfrank R.W., Reihs S., Hug M.
Tetrahedron Letters ,
1993
65.
68
N. N. Mel'nikov
Zhur. Obshch. Khim. ,
1946
66.
Hamamoto M., Nakayama K., Nishiyama Y., Ishii Y.
Journal of Organic Chemistry ,
1993
67.
Che C., Cheng W.
Journal of the Chemical Society Chemical Communications ,
1986
68.
Tai A.F., Margerum L.D., Valentine J.S.
Journal of the American Chemical Society ,
1986
69.
Ishii Y., Yamawaki K., Yoshida T., Ura T., Ogawa M.
Journal of Organic Chemistry ,
1987
70.
Koola J.D., Kochi J.K.
Inorganic Chemistry ,
1987
71.
Mimoun H., Mignard M., Brechot P., Saussine L.
Journal of the American Chemical Society ,
1986
72.
Mimoun H., Saussine L., Daire E., Postel M., Fischer J., Weiss R.
Journal of the American Chemical Society ,
1983
73.
Samsel E.G., Srinivasan K., Kochi J.K.
Journal of the American Chemical Society ,
1985
74.
Srinivasan K., Michaud P., Kochi J.K.
Journal of the American Chemical Society ,
1986
75.
McDonald R.N., Steppel R.N.
Journal of Organic Chemistry ,
1970
76.
Hirao T., Moriuchi T., Mikami S., Ikeda I., Ohshiro Y.
Tetrahedron Letters ,
1993
77.
Chan C., Che C., Peng S.
Polyhedron ,
1993
78.
Gable K.P., Phan T.N.
Journal of the American Chemical Society ,
1994
79.
82
G. P. Brin
Biokhimiya ,
1957
80.
Guerrero A.F., Kim H., Schlecht M.F.
Tetrahedron Letters ,
1988
81.
Agarwal D.D., Bhatnagar R.P., Jain R., Srivastava S.
Journal of Molecular Catalysis ,
1990
82.
85
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1947
83.
Agarwal D.D., Bhatnagar R.P., Jain R., Srivastava S.
Journal of the Chemical Society Perkin Transactions 2 ,
1990
84.
87
J. F. Arens
"Advances in Organic Chemistry" ,
1960
85.
88
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1946
86.
89
A. A. Krasnovskii
Izd. Akad. Nauk SSSR, Moscow ,
1955
87.
90
V. B. Evstigneev
Dokl. Akad. Nauk SSSR ,
1951
88.
Khenkin A.M., Hill C.L.
Journal of the American Chemical Society ,
1993
89.
92
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR ,
1948
90.
Cheng W., Yu W., Cheung K., Che C.
Journal of the Chemical Society Dalton Transactions ,
1994
91.
Che C., Li C., Tang W., Yu W.
Journal of the Chemical Society Dalton Transactions ,
1992
92.
Upadhyay M.J., Bhattacharya P.K., Ganeshpure P.A., Satish S.
Journal of Molecular Catalysis ,
1994
93.
Goldstein A.S., Beer R.H., Drago R.S.
Journal of the American Chemical Society ,
1994
94.
97
A. N. Terenin
Dokl. Akad. Nauk SSSR ,
1952
95.
Weber L., Hommel R., Behling J., Haufe G., Hennig H.
Journal of the American Chemical Society ,
1994
96.
99
V. V. Zolotarev
1938
97.
100
V. V. Zolotarev
Chem. Abs. ,
1941
98.
De Carvalho M., Meunier B.
Tetrahedron Letters ,
1983
99.
Akasaka T., Haranaka M., Ando W.
Journal of the American Chemical Society ,
1993
100.
Tokita Y., Yamaguchi K., Watanabe Y., Morishima I.
Inorganic Chemistry ,
1993
101.
Leung W., Che C., Yeung C., Poo C.
Polyhedron ,
1993
102.
Kwart H., Hoffman D.M.
Journal of Organic Chemistry ,
1966
103.
Kwart H., Starcher P.S., Tinsley S.W.
Chemical Communications (London) ,
1967
104.
Bingham K.D., Meakins G.D., Whitham G.H.
Chemical Communications (London) ,
1966
105.
108
F. Fichter
Helv. Chim. Acta ,
1924
106.
Shackelford S.A., Yuen G.U.
Journal of Organic Chemistry ,
1975
107.
Awasthy A.K., Rocek J.
Journal of the American Chemical Society ,
1969
108.
111
M. Calvin
1956
109.
Traylor T.G., Nakano T., Dunlap B.E., Traylor P.S., Dolphin D.
Journal of the American Chemical Society ,
1986
110.
Traylor T.G., Xu F.
Journal of the American Chemical Society ,
1988
111.
Traylor P.S., Dolphin D., Traylor T.G.
Journal of the Chemical Society Chemical Communications ,
1984
112.
Traylor T.G., Miksztal A.R.
Journal of the American Chemical Society ,
1989
113.
Traylor T.G., Tsuchiya S., Byun Y.S., Kim C.
Journal of the American Chemical Society ,
1993
114.
117
V. V. Levchenko
Zhur. Obshch. Khim. ,
1948
115.
Traylor T.G., Fann W.P., Bandyopadhyay D.
Journal of the American Chemical Society ,
1989
116.
Watanabe Y., Yamaguchi K., Morishima I., Takehira K., Shimizu M., Hayakawa T., Orita H.
Inorganic Chemistry ,
1991
117.
120
V. V. Levchenko
Zhur. Obshch. Khim. ,
1948
118.
Baker R., Halliday D.E.
Journal of the Chemical Society Perkin Transactions 2 ,
1974
119.
Rothberg I., Schneider L., Kirsch S., OFee R.
Journal of Organic Chemistry ,
1982
120.
Adam W., Carballeira N., Crämer E., Peters E., Peters K., Schnering H.G.
Chemische Berichte ,
1987
121.
MacWhorter S.E., Schore N.E.
Journal of Organic Chemistry ,
1991
122.
Lee J., Oh J., Jin S., Choi J., Atwood J.L., Cha J.K.
Journal of Organic Chemistry ,
1994
123.
Lautens M., Crudden C.M.
Tetrahedron Letters ,
1989
124.
125.
Klumpp G.W., Veefkind A.H., De Graaf W.L., Bickelhaupt F.
1967
126.
SOLOWAY S.B., CRISTOL S.J.
Journal of Organic Chemistry ,
1960
127.
Tenaglia A., Terranova E., Waegell B.
Tetrahedron Letters ,
1991
128.
131
N. Thooi
Compt. rend. ,
1958
129.
132
G. Shima
Kyoto Univ. ,
1929
130.
Brown H.C., Hammar W.J., Kawakami J.H., Rothberg I., Vander Jagt D.L.
Journal of the American Chemical Society ,
1967
131.
Christl M., Leininger H., Brunn E.
Journal of Organic Chemistry ,
1982
132.
135
V. V. Korshak
Dokl. Akad. Nauk SSSR ,
1945
133.
Bartlett P.D., Combs G.L., Le A.X., Watson W.H., Galloy J., Kimura M.
Journal of the American Chemical Society ,
1982
134.
137
S. R. Rafikov
Zh. Obshch. Khim. ,
1944
135.
Kwart H., Takeshita T.
Journal of Organic Chemistry ,
1963
136.
Paquette L.A., Carr R.V.
Journal of the American Chemical Society ,
1980
137.
Lerman B.M.
Russian Chemical Reviews ,
1995
138.
Gugelchuk M., Paquette L.A.
Journal of the American Chemical Society ,
1991
139.
Aue D.H., Reynolds R.N.
Journal of the American Chemical Society ,
1973
140.
144
1912
141.
Zalkow L.H., Gabriel S.K.
Journal of Organic Chemistry ,
1969
142.
Paquette L.A., Bellamy F., Wells G.J., Boehm M.C., Gleiter R.
Journal of the American Chemical Society ,
1981
143.
Ohwada T., Okamoto I., Haga N., Shudo K.
Journal of Organic Chemistry ,
1994
144.
148
P. Kresse
Chem. Abs. ,
1960
145.
149
V. V. Korshak
Dokl. Akad. Nauk SSSR ,
1954
146.
150
Ya. E. Bernadskaya
"Iskusstvennoe Volokno" (Artificial Fibres) ,
1952
147.
151
V. M. Rodionov
Zhur. Obshch. Khim. ,
1936
148.
Henbest H.B., Nicholls B.
Journal of the Chemical Society (Resumed) ,
1959
149.
Coates R.M., Williams J.W.
Journal of Organic Chemistry ,
1974
150.
Le Drian C., Vogel P.
Helvetica Chimica Acta ,
1987
151.
Le Drian C., Vogel P.
Helvetica Chimica Acta ,
1988
152.
le Drian C., Vogel P.
Journal of Organic Chemistry ,
1993
153.
Jung M.E., Street L.J.
Tetrahedron Letters ,
1985
154.
Mann J., de Almeida Barbosa L.
Journal of the Chemical Society Perkin Transactions 1 ,
1992
155.
Stille J.K., Kasper P.R., Witherell D.R.
Journal of Organic Chemistry ,
1963
156.
Lehr K., Werp J., Bingmann H., Krüger C., Prinzbach H.
Chemische Berichte ,
1982
157.
161
Friedl.
158.
Brown H.C., Liu K.
Journal of the American Chemical Society ,
1971
159.
163
Friedl.
160.
Suzuki A., Miki M., Itoh M.
Tetrahedron ,
1967
161.
Davis D.D., Johnson H.T.
Journal of Organometallic Chemistry ,
1975
162.
D. Davis D., J. Surmatis A., L. Robertson G.
Journal of Organometallic Chemistry ,
1972
163.
Wilcox C.F.
Journal of the American Chemical Society ,
1960
164.
Gassman P.G., Schaffhausen J.G., Raynolds P.W.
Journal of the American Chemical Society ,
1982
165.
Hoffmann R.W., Hauel N., Landmann B.
Chemische Berichte ,
1983
166.
Fleming I., Michael J.P.
Journal of the Chemical Society Perkin Transactions 1 ,
1981
167.
Baird W.C., Surridge J.H.
Journal of Organic Chemistry ,
1972
168.
Gassman P.G., Marshall J.L.
Journal of the American Chemical Society ,
1966
169.
Matoba Y., Inoue H., Akagi J., Okabayashi T., Ishii Y., Ogawa M.
Synthetic Communications ,
1984
170.
Richey H.G., Moses L.M., Hangeland J.J.
Organometallics ,
1983
171.
Brown H.C., Kawakami J.H., Ikegami S.
Journal of the American Chemical Society ,
1970
172.
176
G. V. Samsonov
"Metody Ispytaniya na Mikrotverdost' i Pribory" (Methods of Microhardness Testing and Apparatus) ,
1965
173.
177
J. Henry
Proc. R. Irish Acad. ,
1945
174.
178
1946
175.
179
Chem. Abs. ,
1947
176.
180
1946
177.
181
Chem. Abs. ,
1947
178.
182
1947
179.
Paddon-Row M.N., Patney H.K., Warrener R.N.
Journal of the Chemical Society Chemical Communications ,
1978
180.
Paddon-Row M.N., Patney H.K., Warrener R.N.
Journal of Organic Chemistry ,
1979
181.
Crandall J.K.
Journal of Organic Chemistry ,
1964
182.
Gergely V., Akhavin Z., Vogel P.
Helvetica Chimica Acta ,
1975
183.
187
1954
184.
Bartlett P.D., Giddings W.P.
Journal of the American Chemical Society ,
1960
185.
Meinwald J., Wiley G.A.
Journal of the American Chemical Society ,
1958
186.
Coxon J., Hartshorn M., Lewis A.
Australian Journal of Chemistry ,
1971
187.
Coxon J., Hartshorn M., Lewis A.
Australian Journal of Chemistry ,
1971
188.
Kleinfelter D.C., Von R. Schleyer P.
Journal of the American Chemical Society ,
1961
189.
Gerteisen T.J., Kleinfelter D.C., Brophy G.C., Sternhell S.
Tetrahedron ,
1971
190.
Palomino E., Schaap A.P., Heeg M.J.
Tetrahedron Letters ,
1989
191.
McDonald R.N., Steppel R.N.
Journal of the American Chemical Society ,
1969
192.
McDonald R.N., Tabor T.E.
Journal of Organic Chemistry ,
1968
193.
197
J. Sicher
Chem. Listy ,
1955
194.
198
W. Cohen
Rec. Trav. chim. ,
1919
195.
199
Yu. K. Delimarskii
Byull. Izobr. ,
1970
196.
Kropp P.J., Worsham P.R., Davidson R.I., Jones T.H.
Journal of the American Chemical Society ,
1982
197.
ApSimon J.W., Yamasaki K., Fruchier A., Chau A.S., Huber C.P.
Canadian Journal of Chemistry ,
1982
198.
202
G. Shiroa
Mem. Coll. Sci., Kyoto Univ. ,
1930
199.
Rehnberg N., Sundin A., Magnusson G.
Journal of Organic Chemistry ,
1990
200.
Vandewalle M., Van der Eycken J., Oppolzer W., Vullioud C.
Tetrahedron ,
1986
201.
Takano S., Kurotaki A., Ogasawara K.
Tetrahedron Letters ,
1987
202.
Shibasaki M., Nishida A., Ikegami S.
Tetrahedron Letters ,
1980
203.
Holton R.A., Kennedy R.M.
Tetrahedron Letters ,
1984
204.
Edelsbacher A., Urban E., Weidenauer W.
Monatshefte fur Chemie ,
1992
205.
209
C. J. Haggerty
Trans. Am. Electrochem. Soc. ,
1929
206.
Lucchini V., Modena G., Pasquato L.
Journal of the Chemical Society Chemical Communications ,
1992
207.
Gray A.P., Heitmeier D.E.
Journal of Organic Chemistry ,
1969
208.
212
L. V. Pavlova
Zh. Obshch. Khim. ,
1965
209.
213
F. Yu. Rachinskii
"Khimiya Seraorganicheskikh Soedinenii, Soderzhashchikh-sya v Neftyakh i Nefteproduktakh" (Chemistry of Organo-sulphur Compounds Present in Petroleum and Petroleum Products) ,
1966
210.
214
L. V. Pavlova
1965
211.
215
N. D. Tomashov
Zh. Prikl. Khim. ,
1970
212.
216
A. P. Tomilov
Zhur. Prikl. Khim. ,
1959
213.
217
1925
214.
218
Chem. Zentr. II ,
1925
215.
Gagneux A., Grob C.A.
Helvetica Chimica Acta ,
1959
216.
Meinwald J., Labana S.S., Chadha M.S.
Journal of the American Chemical Society ,
1963
217.
221
1960
218.
Murray R.W., Pillay M.K., Jeyaraman R.
Journal of Organic Chemistry ,
1988
219.
Baxter A.D., Roberts S.M., Scheinmann F., Wakefield B.J., Newton R.F.
Journal of the Chemical Society Chemical Communications ,
1983
220.
Niwayama S., Kobayashi S., Ohno M.
Tetrahedron Letters ,
1988
221.
Ohno M., Ito Y., Arita M., Shibata T., Adachi K., Sawai H.
Tetrahedron ,
1984
222.
Padwa A., Koehn W.
Journal of Organic Chemistry ,
1973
223.
Weitemeyer C., Preuß T., de Meijere A.
Chemische Berichte ,
1985
224.
Klein H., Kursawa W., Grimme W.
Angewandte Chemie ,
1973
225.
Klein H., Grimme W.
Angewandte Chemie ,
1974
226.
Paquette L.A., Hertel L.W., Gleiter R., Boehm M.C., Beno M.A., Christoph G.G.
Journal of the American Chemical Society ,
1981
227.
Poos G.I., Rosenau J.D.
Journal of Organic Chemistry ,
1963
228.
232
Chem. Abs. ,
1960
229.
233
P. Cotter
J. Am. Chem. Soc. ,
1956
230.
234
Ebach E A
Chem. Abs. ,
1966
231.
235
R. Peffen
1967
232.
Shields T.C.
Canadian Journal of Chemistry ,
1971
233.
237
P. Peshev
Rev. internat. hautes Temperat. et Réfract. ,
1969
234.
238
Brown G P
Am. Chem. Soc., Polymer Preprints ,
1964
235.
239
Mendelbaum H. G.
Bull. Soc. chim. France ,
1973
236.
Jahn H., Raubach H., Rodekirch G., Teige W.
Journal für praktische Chemie ,
1968
237.
241
M. S. Kharasch
"Grignard Reactions of Nonmetallic Substances" ,
1954
238.
242
N. N. Seroenov
"O Nekotorykh Problemakh Khimicheskoi Kinetiki i Reaktsionnoi Sposobnosti" (Some Problems in Chemical Kinetics and Reactivity) ,
1958
239.
243
G. A. Kudintseva
1958
240.
244
C. Wilson
Record. Chem. Prog. ,
1949
241.
245
G. A. Meerson
1958
242.
246
G. A. Meerson
Byull. Izobr. ,
1968
243.
Paulson D.R., Murray A.S., Fornoret E.J.
Journal of Organic Chemistry ,
1978
244.
Hyman M.G., N. M., Paddon-row, Warrener R.N.
Synthetic Communications ,
1975
245.
O'Brien D.F., Gates J.W.
Journal of Organic Chemistry ,
1965
246.
Marchand A.P., Madhusudhan Reddy G., Watson W.H., Kashyap R.
Tetrahedron ,
1990
247.
Toda F., Tanaka K., Marks D., Goldberg I.
Journal of Organic Chemistry ,
1991
248.
Paquette L.A., Carr R.V., Arnold E., Clardy J.
Journal of Organic Chemistry ,
1980
249.
253
D. Goerrig
Chem. Abs. ,
1959
250.
254
M. G. Safarov
1975
251.
Cochrane W.P., Forbes M.A.
Canadian Journal of Chemistry ,
1971
252.
256
Z. V. Zvonkova
Zh. Strukt. Khim. ,
1977
253.
Cella J.A., Kelley J.A., Kenehan E.F.
Journal of Organic Chemistry ,
1975
254.
Macaluso A., Hamer J.
Journal of Organic Chemistry ,
1967
255.
Meinwald J., Seidel M.C., Cadoff B.C.
Journal of the American Chemical Society ,
1958
256.
Block E., Wall A.
Journal of Organic Chemistry ,
1987