Heterophosphacyclanes in organic synthesis

Russian Chemical Reviews

Volumn 63, Issue 12, 1994, Pages 1019-1045

  Cherkasov, Rafael A ^a   Pudovik, Michael A ^b  

^a KAZAN FEDERAL UNIVERSITY   (Russian Federation)

^b A E ARBUZOV INSTITUTE OF ORGANIC AND PHYSICAL CHEMISTRY   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 34250766388     PISSN: 0036021X     EISSN: 14684837     Source Type: Journal    
DOI: 10.1070/RC1994v063n12ABEH000132     Document Type: Article

References (187)

1. Galkin V I, Sayakhov R D, Mironov V A, Kutyrev G A, Cherkasov R A 1993 Zh. Obshch. Khim.63 2476
2. Cadogan J I G (Ed.) 1979 Organophosphorus Reagents in Organic Synthesis (New York: Academic Press)
3. Cherkasov R A, Kutyrev G A, Pudovik A N 1985 Tetrahedron41 2567 13
4. Cava M P, Levinson M I 1985 Tetrahedron41 5061 22
5. Mitsunobu O 1981 Synthesis1981 1 1
6. Akita H, Yamada H, Matsukura H, Nakata T, Oishi T 1990 Tetrahedron Lett.31 1781
7. Minami T, Motoyoshiyo J 1992 Synthesis1992 333 4
8. Kagan H B 1982 Comprehensive Organometallic Chemistry vol 8 (Oxford: Pergamon Press) p 463
9. Brunner H, Pieronczyk W, Schoenhammer B, Streng K, Bernal I, Korp J 1981 Chem. Ber.114 1137 3
10. Germa H, Navech J 1986 Phosphorus Sulfur26 327 3
11. Vestheimer F H 1981 Chem. Rev.81 313 4
12. Baccolini G, Todesco P E 1983 J. Chem. Soc. Perkin Trans 11983 535
13. Cabral J, Laszlo P, Montaufier M-T, Randriamahefa S L 1990 Tetrahedron Lett.31 1705 12
14. Pudovik M A, Ovchinnikov V V, Cherkasov R A, Pudovik A N 1983 Usp. Khim.52 640
15. Pudovik M A, Ovchinnikov V V, Cherkasov R A, Pudovik A N 1983 Russ. Chem. Rev.52 361 4
16. Cherkasov R A, Ovchinnikov V V, Pudovik M A, Pudovik A N 1982 Usp. Khim.51 1305 8
17. Cherkasov R A, Ovchinnikov V V, Pudovik M A, Pudovik A N 1982 Russ. Chem. Rev.51 746 8
18. Polezhaeva N A, Cherkasov R A 1985 Usp. Khim.54 1899 11
19. Polezhaeva N A, Cherkasov R A 1985 Russ. Chem. Rev.54 1126 11
20. Cherkasov R A, Polezhaeva N A 1987 Usp. Khim.56 287 2
21. Cherkasov R A, Polezhaeva N A 1987 Russ. Chem. Rev.56 163 2
22. Regitz M, Maas G 1981 Organic Chemistry (Berlin) p 71
23. Markovskii L N 1990 Izv. Akad. Nauk SSSR, Ser. Khim. 2305
24. Patsanovskii I I, Ishmaeva E A 1993 Zh. Obshch. Khim.63 2552
25. Cadogan J I G, Cowley A H, Gosney I, Pakulski M, Wright P M, Yaslac S 1986 J. Chem. Soc. Chem. Commun. 1685
26. Banks M R, JICadogan G, Gosney I, Hadson P K G, Rodger D R 1990 Phosphorus Sulfur49/50 381 1
27. Banks M R, Cadogan J I G, Gosney I, Hadson P K G, Rodger D R 1989 J. Chem. Soc. Chem. Commun. 1033
28. Ingold C K 1973 Structure and Mechanism in Organic Chemistry (Translated into Russian Moscow: Mir) p 615
29. Osipova M P, Volkova R V, Zlobina A I 1985 Zh. Obshch. Khim.55 697
30. Nifant'ev E E, Zavalishina A I, Sorokina S F, Borisenko A A 1976 Zh. Obshch. Khim.46 471
31. Kim S, Roundhilt D M 1992 Phosphorus Sulfur70 3 1
32. Pudovik A N, Pudovik M A, Terent'eva S A, Bel'skii V E 1971 Zh. Obshch. Khim.41 2407
33. Pudovik M A, Terent'eva S A, Pudovik A N 1981 Zh. Obshch. Khim.51 518
34. Pudovik M A, Pudovik A N 1973 Zh. Obshch. Khim.43 2144
35. Hassner A, Alexanian V 1979 J. Org. Chem.44 3861 22
36. Pudovik A N, Pudovik M A, Ivanova L K 1971 Zh. Obshch. Khim.41 2677
37. Pudovik A N, Pudovik M A, Shulyndina O S 1970 Zh. Obshch. Khim.40 501
38. Terent'eva S A, Pudovik M A, Pudovik A N 1979 Izv. Akad. Nauk SSSR, Ser. Khim.49 1152
39. Mukajama T, Kuvajima J, Suzuki Z 1963 J. Org. Chem.28 2024 8
40. Gloede J 1991 Phosphorus Sulfur55 255 1
41. Pudovik M A, Pudovik A N 1975 Izv. Akad. Nauk SSSR, Ser. Khim. 964
42. Mironov V F, Mavleev R A, Ofitserov E N, Sinyashina T A, Konovalov I V, Pudovik A N 1991 Izv. Akad. Nauk SSSR, Ser. Khim. 1676
43. Mironov V F, Konovalova I V, Mavleev R A, Mukhtarov A Sh, Ofitserov E N, Pudovik A N 1991 Zh. Obshch. Khim.61 2150
44. Mironov V F, Burnaeva L A, Konovalova I V, Khlopushina G A, Mavleev R A, Chernov P P, Pudovik A N 1993 Zh. Obshch. Khim.63 25
45. Mironov V F, Burnaeva L A, Konovalova I V, Khlopushina G A, Chernov P P 1993 Zh. Org. Khim.29 639
46. Mironov V F, Burnaeva L A, Krokhalev V M, Saloutin V I, Konovalova I V, Mavleev R A, Chernov P P 1992 Zh. Obshch. Khim.62 1425
47. Konovalova I V, Mironov V F, Burnaeva L A, Krokhalev V M, Saloutin V I 1993 Tez. Dokl. IX Mezhdunar. Simp, po Khimii Fosfora, Sankt-Peterburg (Abstracts of Reports at the IXth International Symposium on the Chemistry of Phosphorus) (St Petersburg) p 48
48. Black T H, Arrivo S M, Schumm J S, Knobeloch J M 1986 J. Chem. Soc. Chem. Commun.1986 1524 20
49. Black T H, Arrivo S M, Schumm J S, Knobeloch J M 1987 J. Org. Chem.52 5425 24
50. Mironov V F, Mavleev R A, Ofitserov E N, Pudovik A N 1991 J. Fluorine Chem.54 299 1-3
51. Mironov V F, Mavleev R A, Konovalova I V, Pudovik A N 1991 Zh. Obshch. Khim.61 1259
52. Mikolajchyk M, Luczak J 1988 Zh. Obshch. Khim.58 2024
53. Mikolajczyk M, Luczak J 1978 J. Org. Chem.43 2132 11
54. Dreux M, Leroux G, Savignac Ph 1974 Synthesis1974506 7
55. Miller H B, Baird H W, Bramlett C L, Templeton W K 1976 J. Chem. Soc. Chem. Commun.1976 262
56. Chaus M P, Gusar' N I, Gololobov Y. G 1983 Zh. Obshch. Khim.53 244
57. Armour M-A, JICadogan G, Grace D S 1975 J. Chem. Soc. Perkin Trans 21975 1185 11
58. Burski J, Kieszkowski J, Michalski J, Pakulski M, Skowronska A 1983 Tetrahedron39 4175 24
59. Burski J, Kieszkowski J, Michalski J, Pakulski M, Skowronska A 1978 J. Chem. Soc. Chem. Commun.1978 940 21
60. Krawczyk E, Michalski J, Pakulski M 1977 Tetrahedron Lett.18 2019 23
61. Isaev V L, Mal'kovich L Yu, Sterlin R N, Knunyants I L 1974 Zh. Vses. Khim. O-va im D I Mendeleeva19 586
62. Kimura H, Konno H, Takahashi N 1982 Bull. Chem. Soc. Japan.66 327 1
63. S Hanessian, Y Leblanc, P Lavallee Tetrahedron Lett23 4411
64. Eisenhut M, Schmutzler R 1974 Phosphorus4 73
65. Das V K, Zucherman J J 1971 Inorg. Chem.10 1028 5
66. Cros P, Buono G, Peiffer G, Denis D, Mortreux A, Petit F 1987 New J. Chem.11 573
67. Arzoumanian H, Buono G, Choukrad M, Petrignani J F 1988 Organometallics7 59 1
68. Alexakis A, Mutti S, Normand J F 1991 J. Am. Chem. Soc.113 6332 16
69. Buono G, Brunei J-M, Faure B, Pardigow G 1993 Phosphorus Sulfur75 43 1
70. Bontragy J, Thomas R 1974 Chem. Rev.74 87 1
71. Wadsworth W S 1977 Org. React.25 73
72. Maryanoff B E, Reitz A B 1989 Chem. Rev.89 900 4
73. Quin L D, Sadanani N D, Bourdieu K, X-P Wu, Quin G S, Bodalski R 1990 Phosphorus Sulfur49/50 313 1
74. Quin L D, Marsi B G 1985 J. Am. Chem. Soc.107 3389 11
75. Quin L D, Szewczyk J, Szewczyk K M, McPail A T 1986 J. Org. Chem.51 3341 17
76. Quin L D, Pete B, Szewczyk J, Mughes A N 1988 Tetrahedron Lett.29 2627 22
77. Quin L D, Sadanani N D, X-P Wu 1989 J. Am. Chem. Soc.111 6852 17
78. Quin L D, Bourdien C, Quin G S 1990 Tetrahedron Lett.31 6473 45
79. Sigal J, Loew L 1978 J. Am. Chem. Soc.100 6394 20
80. Tomioka H, Watanabe M, Kobayashi N, Nirai K 1990 Tetrahedron Lett.31 5061 35
81. Nifant'ev E E, Predvoditelev D A 1994 Usp. Khim.63 73
82. Nifant'ev E E, Predvoditelev D A 1994 Russ. Chem. Rev.63 71 1
83. Kukhar' V P, Svistunova N Yu, Solodenko V A, Soloshonok V A 1993 Usp. Khim.62 284 3
84. Kukhar' V P, Svistunova N Yu, Solodenko V A, Soloshonok V A 1993 Russ. Chem. Rev.62 261 3
85. Givens R S, Kueper W 1993 Chem. Rev.93 55 1
86. Kutyrev G A, Lygin A V, Cherkasov R A, Pudovik A N 1982 Zh. Obshch. Khim.52 501
87. Kutyrev G A, Lygin A V, Cherkasov R A, Konovalova I V, Pudovik A N 1983 Zh. Obshch. Khim.53 1213
88. Kutyrev G A, Kutyrev A A, Cherkasov R A, Pudovik A N 1982 Phosphorus Sulfur13 135 2
89. Kutyrev G A, Cherkasov R A 1984 Usp. Khim.53 1675 10
90. Kutyrev G A, Cherkasov R A 1984 Russ. Chem. Rev.53 971 10
91. Baraniak J, Stec W 1991 Tetrahedron Lett.32 4193 33
92. Stiell W C, Gennari C 1983 Tetrahedron Lett.24 4405 41
93. Thomson S K, Heathcock C H 1990 J. Org. Chem.55 3386 10
94. Broeckman K K Jr, Weidner C H, Perni R B, Napier J J 1989 J. Am. Chem. Soc.111 8036 20
95. Bottin-Stzalko T, Seyden-Penne J, Brener E, Pouet M J, Simonnin M-P 1985 J. Chem. Soc. Perkin Trans. 21985 1801 11
96. Denmark S E, Cramer C J 1990 J. Org. Chem.55 1806 6
97. Denmark S E, Miller P C, Wilson S R 1991 J. Am. Chem. Soc.113 1468 4
98. Patois C, Ricard L, Savignac P 1990 J. Chem. Soc. Perkin Trans. 11990 1577 6
99. Larsen R O, Aksness G 1983 Phosphorus Sulfur15 219 2
100. Tessier J 1986 Actual. Chim.5
101. Hanessian S, Delorme D, Beaudoin S, Leblanc Y 1984 J. Am. Chem. Soc.106 5754 19
102. Patois C, Savignac P 1991 Tetrahedron Lett.32 1317 10
103. Patois C, Savignac P 1991 Synlett.1991517 7
104. Patois C, Savignac P 1993 Phosphorus Sulfur75 143 1
105. Savignac P, Tenlade M P, Patois C 1990 Phosphorus Sulfur49/50 169 1
106. Longmire C F, Evans S A Jr 1990 J. Chem. Soc. Chem. Commun.1990922 13
107. Gordon N J, Evans S A Jr 1993 Phosphorus Sulfur75 47 1
108. Hua D H, Chan-King Ju-, McKie J A, Myer L 1987 J. Am. Chem. Soc.109 5026 16
109. Denmark S E, Martin J E 1987 J. Org. Chem.52s 42
110. Denmark S E, Rajendra G, Martin J E 1989 Tetrahedron Lett.30 2469 19
111. Denmark S E, Martin J E 1991 J. Org. Chem.56 1003 3
112. Kumaras K C, Burton S D, Holmes J M, Day R O, Holmes R R 1990 Phosphorus Sulfur53 437 1
113. Gloede J 1982 Z. Chem.22 126 4
114. Kluger R, Taylor S D 1991 J. Am. Chem. Soc.113 996 3
115. Breslow R, Anglyw E, Deen-Lih Huang 1991 Tetrahedron47 2365 14-15
116. Bestmann H J 1979 Pure Appl. Chem.51 515 3
117. WMcEwen E, Bearer B D, Conney J V 1985 Phosphorus Sulfur25 255 3
118. Ward W G Jr, McEven W E 1990 J. Org. Chem.55 493 2
119. BMaryanoff E, Reitz A B, Mutter M S, Inners R R, Almond H A, Whittle R R, Olofson R A 1986 J. Am. Chem. Soc.108 7664 24
120. Meanwell N A, Roth H R, Smith E C R, Wedding D L, Kim Wright J J 1991 J. Org. Chem.56 6897 24
121. Kawashita T, Kato K, Okaraki R 1992 J. Am. Chem. Soc.114 4008 10
122. Kolodyazhnyi O I 1986 Zh. Obshch. Khim.56 283
123. Granoth I, Martin J C 1979 J. Am. Chem. Soc.101 4618 16
124. Kolodyazhnyi O I, Kukhar' V P 1983 Usp. Khim.52 1903
125. Kolodyazhnyi O I, Kukhar' V P 1983 Russ. Chem. Rev.52 1096 11
126. Kolodyazhnyi O I 1991 Usp. Khim.60 799 4
127. Kolodyazhnyi O I 1991 Russ. Chem. Rev.60 391 4
128. Kolodyazhnyi O I, Golokhov D B 1988 Zh. Obshch. Khim.58 490
129. Kolodyazhnyi O I, Golokhov D B 1989 Zh. Obshch. Khim.59 293
130. Hercouet A, LeCorre M 1981 Tetrahedron37 2861 16
131. Hercouet A, LeCorre M 1981 Tetrahedron37 2855 16
132. Hercouet A, LeCorre M 1981 Tetrahedron37 2867 16
133. Abell A D, Morris K B, Litten J C 1990 J. Org. Chem.55 5217 18
134. BMaryanoff E, Reitz A B, Duhl-Emswiler A D 1983 Tetrahedron Lett.24 2477 24
135. Reitz A B, Maryanoff B E 1984 J. Chem. Soc. Chem. Commun.1984 1548 23
136. Maryanoff B E, Reitz A B, Duhl-Emswiler A D 1985 J. Am. Chem. Soc.107 217 1
137. Enholm E J, Satici H, Prasad G 1990 J. Org. Chem.55 324 1
138. Boudia B, Mann A, Bellamy F D, Mioskowski C 1990 Angew. Chem.102 1522 12
139. Schmidpeter A, Criegern T 1978 Chem. Ber.111 3747 11
140. Ramirez F 1974 Synthesis1974 90 2
141. Ramirez F 1973 Pure Appl. Chem.1973185
142. Konovalova I V, Yudina T V, Ofitserova E Kh, Anoshina N P, Pudovik A N 1978 Zh. Obshch. Khim.48 1936
143. Willson M, Burgada R, Mathis F 1975 Bull. Soc. Chim Fr.2241
144. Leroux G, Monouni D E, Burgada R 1981 Tetrahedron Lett.22 3393 35
145. Hund H, Roschenthaler G-V 1991 Phosphorus Sulfur62 71 1
146. McClure C K, Jung K-Y 1991 J. Org. Chem.56 2326 7
147. McClure C K, Jung K-Y, Grote C W, Hangen K 1993 Phosphorus Sulfur75 23 1
148. McClure C K, Jung K-Y, Grote C W 1990 Phosphorus Sulfur51/52 418 1
149. McClure C K, Jung K-Y 1991 J. Org. Chem.56 867 2
150. Fang F G, Maier M E, Danishefski S J, Schulte G 1990 J. Org. Chem.55 831 3
151. Mikolajczyk M, Zatorski A 1991 J. Org. Chem.56 1217 3
152. Gazizov T Kh, Belyalov R U, Pudovik A N 1982 Zh. Obshch. Khim.52 487
153. Arbuzov B A, Vizel' A O, Shchukina L I, Vakulenko O V, Zyablikova T A, Krupnov V K, Zyryanova L I 1985 Zh. Obshch. Khim.55 1705
154. Mizrakh L I, Polonskaya L Yu, Gvozdetskii A N, Karpunina L B 1990 Zh. Obshch. Khim.60 1422
155. Mizrakh L I, Polonskaya L Yu, Gvozdetskii A N, Vasil'ev A M 1986 Zh. Obshch. Khim.56 73
156. Burgada R, Mohri A, Khoshnieh Y El C 1979 R. Hebd. Seances Acad. Sci. Ser C 288 165
157. Burgada R, Mohri A 1982 Phosphorus Sulfur13 85 1
158. Rybinskaya M I 1978 Koord. Khim.4 3
159. Scheeren J W, Brown P M 1975 Synthesis1975 527 8
160. Mironov V F, Ofitserov E N, Sinyashina T N, Konovalova I V 1990 Zh. Obshch. Khim.26 2570
161. Pudovik M A, Kibardina L I, Pudovik A N 1991 Zh. Obshch. Khim.61 604
162. Kawamota N, Kawaji H, Nitta M 1992 J. Org. Chem.57 618 2
163. Husband J B, McNab H 1984 Phosphorus Sulfur20 207 2
164. Denney B D, Denney D Z, Gigantio J J 1984 J. Org. Chem.49 2831 15
165. Kelly J W, Evans S A 1986 J. Org. Chem.51 5490 26
166. Kelly J W, Robinson P L, Evans S A 1985 J. Org. Chem.50 5007 24
167. PRobinson L, Barry C N, Kelly J W, Evans S A 1985 J. Am. Chem. Soc.107 5210 18
168. Robinson P L, Evans S A 1985 J. Org. Chem.50 3860 20
169. PRobinson L, Kelly J W, Evans S A 1986 Phosphorus Sulfur26 15 1
170. Barry C N, Evans S A 1981 J. Org. Chem.46 3361 16
171. Murray W T, Evans S A 1989 J. Org. Chem.54 2440 10
172. Murray W T, Pautard-Cooper A, Eshew N A, Evans S A 1990 Phosphorus Sulfur49/50 101 1
173. Kelly J W, Evans S A 1986 J. Am. Chem. Soc.108 7681 24
174. PRobinson L, Barry C N, Bass S W, Jarvis S E, Evans S A 1983 J. Org. Chem.48 5396 26
175. Kelly J W, Robinson P L, Evans S A 1986 J. Org. Chem.51 4473 23
176. Murray W T, Kelly J W, Evans S A 1987 J. Org. Chem.52 525 4
177. Kelly J W, Eskew N L, Evans S A 1986 J. Org. Chem.51 95 1
178. Willeit A, Muller E P, Peringer P 1983 Helv. Chim. Acta66 2467 8
179. Pochlauer P, Muller E P, Peringer P 1984 Helv. Chim. Acta67 1238 5
180. Muller E P 1982 Helv. Chim. Acta65 1617 5
181. Himmer C, Peringer P, Muller E P 1990 Phosphorus Sulfur51/52 335 1
182. Pautard A, Evans S A 1988 J. Org. Chem.53 2300 10
183. Pautard A, Evans S A 1989 J. Org. Chem.54 2485 10
184. Pautard A, Evans S A 1989 J. Org. Chem.54 4974 20
185. Pautard A, Evans S A, Kenan W P 1991 Tetrahedron47 1603 9
186. Matheien-Pelta J, Evans S A 1992 J. Org. Chem.57 3409 12
187. Matheien-Pelta J, Evans S A 1993 Phosphorus Sulfur77 219