REACTIONS OF PHOSPHINES WITH ACETYLENES .18. MECHANISM OF FORMATION OF 1,2-ALKYLIDENEDIPHOSPHORANES

被引:63
作者
TEBBY, JC [1 ]
WILSON, IF [1 ]
GRIFFITHS, DV [1 ]
机构
[1] UNIV KEELE,DEPT CHEM,KEELE ST5 5BG,STAFFORDSHIRE,ENGLAND
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1979年 / 09期
关键词
D O I
10.1039/p19790002133
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reactions of dimethyl acetylenedicarboxylate and dibenzoylacetylene with a variety of tertiary arylphosphines, in excess, have been studied. Evidence is presented to show that 1,2-alkylidenediphosphoranes are formed via zwitterionic intermediates which have the character of nucleophilic carbenes. 1,2- Bismethoxycarbonyl-2-thioxoethylidenetriphenylphosphorane and 1,2-dibenzoyl-2-thioxoethylidenetriphenylphosphorane have been isolated by trapping the intermediate with sulphur.
引用
收藏
页码:2133 / 2135
页数:3
相关论文
共 21 条
[1]   RESEARCHES ON ACETYLENIC COMPOUNDS .1. THE PREPARATION OF ACETYLENIC KETONES BY OXIDATION OF ACETYLENIC CARBINOLS AND GLYCOLS [J].
BOWDEN, K ;
HEILBRON, IM ;
JONES, ERH ;
WEEDON, BCL .
JOURNAL OF THE CHEMICAL SOCIETY, 1946, (JAN) :39-45
[2]   METHODS OF DISTINGUISHING BETWEEN CYANO-STABILIZED IMINO-PHOSPHORANES AND METHYLENE-PHOSPHORANES - CRYSTAL-STRUCTURES OF ADDUCTS FROM TRIPHENYLPHOSPHINE AND TETRACYANOETHYLENE (A HEPTACYANOCYCLOPENTENYLIMINOPHOSPHORANE) AND FROM TRIPHENYLPHOSPHINE AND DICYANOACETYLENE (A HEXACYANOHEXA-1,6-DIENEDIPHOSPHORANE) [J].
BUTTERFIELD, PJ ;
TEBBY, JC ;
KING, TJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1978, (10) :1237-1243
[3]   REACTIONS OF PHOSPHINES WITH ACETYLENES .17. FORMATION AND STEREOCHEMISTRY OF 1,2-DICYANO-2-PHOSPHONIAETHANESULPHONATE BETAINES [J].
BUTTERFIELD, PJ ;
TEBBY, JC ;
GRIFFITHS, DV .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (05) :1189-1191
[4]  
DUPONT G, 1913, ANN CHIM, V30, P507
[5]  
FREEMAN BH, 1974, TETRAHEDRON, V30, P211, DOI 10.1016/S0040-4020(01)97237-0
[6]   Studies in the polyene series part XIII Acetylenyl glycols from polyene aldehydes and their rearrangement wbth acids [J].
Heilbron, IM ;
Jones, ERH ;
Raphael, RA .
JOURNAL OF THE CHEMICAL SOCIETY, 1944, :136-139
[7]   PHOSPHONIUM SALT FORMATION OF 2ND KIND [J].
HOFFMANN, H ;
DIEHR, HJ .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1964, 3 (11) :737-&
[8]   GENERATION OF CARBENES BY THERMAL CYCLOELIMINATION [J].
HOFFMANN, RW .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1971, 10 (08) :529-+
[9]  
Johnson A.W., 1966, YLID CHEM
[10]   ADDUCTS FROM TRIPHENYLPHOSPHINE AND DIMETHYL ACETYLENEDICARBOXYLATE [J].
JOHNSON, AW ;
TEBBY, JC .
JOURNAL OF THE CHEMICAL SOCIETY, 1961, (MAY) :2126-&