ORGANOPHOSPHORUS COMPOUNDS .48. 1-HALOGEN-1H-PHOSPHIRENES FROM PHOSPHAALKYNES AND CHLOROCARBENES

被引：30

作者：

WAGNER, O ^{[1
]}

EHLE, M ^{[1
]}

BIRKEL, M ^{[1
]}

HOFFMANN, J ^{[1
]}

REGITZ, M ^{[1
]}

机构：

[1] UNIV KAISERSLAUTERN,FACHBEREICH CHEM,ERWIN SCHRODINGER STR,W-6750 KAISERSLAUTERN,GERMANY

来源：

CHEMISCHE BERICHTE | 1991年 / 124卷 / 05期

关键词：

DIAZIRINES; PHOSPHAALKYNES; CARBENES; PHOSPHORENES; 2+1] CYCLOADDITION;

D O I：

10.1002/cber.19911240538

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Halogen-substituted carbenes (7a-i), generated by thermolysis of diazirines (11a-i), add onto phosphaalkynes (8a-c) to form the title compounds (10a-1). Initially formed 2H-phosphirenes (9) could not be detected as their subsequent conversion to the 1H-isomers 10 by a 1,3-halogen shift is very fast. Hydrolysis of 10c,e,g-i and k yields vinylphosphonous acids (17a-e). 1-Chloro-1H-phosphirenes are transformed by nucleophilic substitution into fluoro (10a,c,e --> 19a-c), bromo (10c,e --> 20a,b), and iodo analogs (10c,e --> 21a,b) with the help of silver tetrafluroborate, trimethylsilyl bromide, and trimethylsilyl iodide, respectively. A crystal structure analysis of 10 c is reported.

引用

页码：1207 / 1213

页数：7

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