REACTIONS OF YLIDES FORMED FROM TRIALKYL PHOSPHITES WITH DIALKYL ACETYLENEDICARBOXYLATES IN THE PRESENCE OF CARBON-DIOXIDE

被引：23

作者：

CAESAR, JC

GRIFFITHS, DV

GRIFFITHS, PA

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 | 1990年 / 08期

关键词：

D O I：

10.1039/p19900002329

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The ylides (2) ⇌ (3) formed from trialkyl phosphites and dialkyl acetylenedicarboxylates in the presence of carbon dioxide react with proton donors, such as phenol or diethylamine, to give stabilised ylides (4). With water, proton transfer within the stabilised ylide results in the formation of a quasiphosphonium salt (6) which can then cyclise to a 1,2-oxaphospholane (7) or dealkylate to give phosphorates (5). In some cases, hydrolysis of the ylide (2) ⇌ (3) occurs to give phosphate and an acid (9). The formation of a furan (12) during the reaction of the ylide (2) ⇌ (3) with 4-nitrobenzaldehyde has been investigated.

引用

页码：2329 / 2334

页数：6

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