NOVEL QUASIPHOSPHONIUM YLIDES FROM THE REACTION OF TRIALKYL PHOSPHITES WITH DIALKYL BENZOYLPHOSPHONATES - EVIDENCE FOR CARBENE INTERMEDIATES IN THE INTRAMOLECULAR CYCLIZATION OF 2-SUBSTITUTED DIALKYL BENZOYLPHOSPHONATES

被引：23

作者：

GRIFFITHS, DV

GRIFFITHS, PA

WHITEHEAD, BJ

TEBBY, JC

机构：

[1] UNIV KEELE,DEPT CHEM,KEELE ST5 5BG,STAFFS,ENGLAND

[2] STAFFORDSHIRE POLYTECH,DEPT APPL SCI,STOKE ON TRENT ST4 2DE,STAFFS,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1992年 / 04期

关键词：

D O I：

10.1039/p19920000479

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of dialkyl aroylphosphonates 1 with trialkyl phosphites leads to the formation of novel quasiphosphonium ylides 4 which in some cases thermally rearrange to the bisphosphonates 5. 2-Substituted dialkyl aroylphosphonates may also undergo intramolecular cyclisation under these conditions. Evidence is presented for the involvement of the carbene intermediates 3.

引用

收藏

页码：479 / 484

页数：6

相关论文

共 9 条

[1] REACTIONS OF AROYL HALIDES WITH PHOSPHITES . ESTERS OF AROYLPHOSPHONIC ACIDS [J].

BERLIN, KD ;

TAYLOR, HA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (18) :3862-&

[2]

BESTMANN HJ, 1976, ORGANIC PHOSPHORUS C, V3, pCHA5

[3]

CADOGAN JIG, 1979, ORGANOPHOSPHORUS REA, P304

[4] RING-FORMING DEOXYGENATION OF ORTHO-SUBSTITUTED AROYLPHOSPHONIC DIESTERS [J].

CHIUSOLI, GP ;

COMETTI, G ;

BELLOTTI, V .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1977, (07) :216-217

[5] THE PREPARATION OF SOME ALKYL-SUBSTITUTED BENZOIC ACIDS [J].

CRAWFORD, M ;

STEWART, FHC .

JOURNAL OF THE CHEMICAL SOCIETY, 1952, (NOV) :4443-4447

[6] CARBENE INTERMEDIATES IN THE REACTION OF TRIALKYL PHOSPHITES WITH DIALKYL AROYLPHOSPHONATES - FORMATION OF NOVEL QUASIPHOSPHONIUM YLIDES [J].

GRIFFITHS, DV ;

TEBBY, JC .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (11) :871-872

[7] REACTIONS OF PHOSPHITES WITH ACID-CHLORIDES - PHOSPHITE ATTACK AT THE CARBONYL OXYGEN OF ALPHA-KETOPHOSPHONATES [J].

GRIFFITHS, DV ;

JAMALI, HAR ;

TEBBY, JC .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1981, 11 (01) :95-99

[8] THE REACTION OF PHOSPHITES WITH AROYLPHOSPHONATES IN THE PRESENCE OF PROTON DONORS REVERSE NUCLEOPHILIC-ADDITION TO CARBONYL GROUPS [J].

GRIFFITHS, DV ;

JAMALI, HAR ;

TEBBY, JC .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1985, 25 (02) :173-175

[9] SYNTHESIS AND NUCLEAR MAGNETIC-RESONANCE SPECTROSCOPY OF SOME SUBSTITUTED ARYLDIAZOALKANEPHOSPHONATES [J].

GURUDATA, N ;

BENEZRA, C ;

COHEN, H .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1973, 51 (07) :1142-1147