FLASH VACUUM PYROLYSIS OF STABILIZED PHOSPHORUS YLIDES .2. 2-STEP CONVERSION OF ACID-CHLORIDES INTO ACETYLENIC ESTERS AND TERMINAL ALKYNES

被引：28

作者：

AITKEN, RA

HORSBURGH, CER

MCCREADIE, JG

SETH, S

机构：

[1] School of Chemistry, University of St. Andrews, St. Andrews, Fife

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1994年 / 13期

关键词：

D O I：

10.1039/p19940001727

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The known thermal extrusion of Ph(3)PO from alpha-acyl-alpha-ethoxycarbonyl ylides 1 to give acetylenic esters 2 can be accomplished in excellent yield by using flash vacuum pyrolysis (FVP) at 500 degrees C. Upon raising the furnace temperature to 750 degrees C, this reaction is accompanied by the unexpected loss of the ethoxycarbonyl group to give the terminal alkynes 7 in moderate yield. A mechanism is proposed for this reaction based on isotopic labelling studies. Ten new examples of ylides 1 have been prepared for the first time.

引用

页码：1727 / 1732

页数：6

共 15 条

[1]

ABELL AD, 1985, SYNTHESIS-STUTTGART, P764

[2]

AITKEN RA, 1990, SYNLETT, P211

[3]

AITKEN RA, UNPUB J CHEM SOC P1

[4]

AITKEN RA, 1994, J CHEM SOC P1