GEM-DIFLUOROCYCLOPROPANES - AN IMPROVED METHOD FOR THEIR PREPARATION

被引：34

作者：

BESSARD, Y ^{[1
]}

MULLER, U ^{[1
]}

SCHLOSSER, M ^{[1
]}

机构：

[1] UNIV LAUSANNE,INST CHIM ORGAN,RUE BARRE 2,CH-1005 LAUSANNE,SWITZERLAND

来源：

TETRAHEDRON | 1990年 / 46卷 / 15期

关键词：

D O I：

10.1016/S0040-4020(01)87828-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

By treatment with dibromodifluoromethane and triphenylphosphine, four unfunctionalized olefins, four enethers and one bis-enether were converted to the gem-difluorocyclopropanes 1- 9. The yields were considerably increased and isomerizations at the double bonds were avoided if the reactions were carried out in the presence of a macrocyclic polyether such as "18-crown-6" and if, in addition, the reagents were employed in moderate excess. © 1990.

引用

页码：5213 / 5221

页数：9

共 25 条

[1]

BIRCHALL JM, 1960, P CHEM SOC LONDON, P81

[2] BASIC BEHAVIOR OF EPOXIDES IN PRESENCE OF HALIDE IONS [J].

BUDDRUS, J .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1972, 11 (12) :1041-1050

[3]

BUDDRUS J, 1972, ANGEW CHEM, V84, P1173

[4]

BUNGE W, 1959, HOUBENWEYL METHODEN, V1, P814

[5] BROMODIFLUOROMETHYLPHOSPHONIUM SALTS - CONVENIENT SOURCE OF DIFLUOROCARBENE [J].

BURTON, DJ ;

NAAE, DG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (25) :8467-8468

[6] TERMINAL UNSATURATION IN POLYPROPYLENE GLYCOL [J].

DEGE, GJ ;

HARRIS, RL ;

MACKENZIE, JS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (13) :3374-3379

[7]

FRITZ HP, 1981, Z NATURFORSCH B, V36, P1375

[8]

HUBERT AJ, 1969, SYNTHESIS-STUTTGART, P97

[9] BASIC BEHAVIOR OF EPOXIDES IN PRESENCE OF HALIDE IONS .4. GEM-DIFLUOROCYCLOPROPANES FROM DIFLUOROCARBENE, GENERATED FROM CHLORODIFLUOROMETHANE AND ALKOXIDE IONS IN SMALL CONCENTRATION [J].

KAMEL, M ;

KIMPENHAUS, W ;

BUDDRUS, J .

CHEMISCHE BERICHTE-RECUEIL, 1976, 109 (07) :2351-2369

[10] STEROIDS .207. STEROIDAL DIHALOCYCLOPROPANES [J].

KNOX, LH ;

LANDIS, PW ;

CROSS, AD ;

VELARDE, E ;

CUADRIELLO, D ;

BERGER, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (12) :1851-&

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