FATTY ACIDS .19. CONVERSION OF ALKENOIC ACIDS TO ALKYNOIC ACIDS BY BROMINATION-DEHYDROBROMINATION

被引：19

作者：

GUNSTONE, FD

HORNBY, GM

机构：

[1] Department of Chemistry, The University of St. Andrews, St. Andrews, Scotland, North Haugh

来源：

CHEMISTRY AND PHYSICS OF LIPIDS | 1969年 / 3卷 / 01期

关键词：

D O I：

10.1016/0009-3084(69)90032-2

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Alkynoic acids (including octadec-9-ynoic, hendec-10-ynoic, and 12-hydroxy-octadec-9-ynoic) can be prepared from the cis alkenoic acids by bromination followed by dehydrobromination with sodium in liquid ammonia or with DBU (1,5-diazabicyclo(5.4.0) undec-5-ene). With other bases extensive migration of the unsaturated centre was observed and no satisfactory procedure for converting trans alkenoic acids to alkynoic acids without migration was discovered. Both types of alkenoic acids could be converted to ene-bromides, sometimes in high yield, with DBU and DBN (1,5-diazabicyclo(4.3.0)non-5-ene). © 1969.

引用

页码：91 / &

共 11 条

[1]

ABBOTT GG, UNPUBLISHED OBSERVAT

[2]

ADKINS H, 1955, ORG SYNTH, V3, P785

[3] ACETYLENIC COMPOUNDS .1. THE DEHYDROHALOGENATION REACTIONS BY SODAMIDE IN LIQUID AMMONIA AND PREPARATION OF SOME MONO-ACETYLENIC SUBSTANCES AND THEIR DERIVATIVES [J].