STEREOCHEMICAL FEATURES OF PALLADIUM-CATALYZED ALLYLIC CARBONYLATION OF ACYCLIC TERPENES

被引:13
作者
KIJI, J
OKANO, T
ONO, I
KONISHI, H
机构
[1] Tottori Univ, Tottori, Jpn, Tottori Univ, Tottori, Jpn
来源
JOURNAL OF MOLECULAR CATALYSIS | 1987年 / 39卷 / 03期
关键词
CATALYSTS - Palladium - ORGANIC COMPOUNDS - Synthesis;
D O I
10.1016/0304-5102(87)80081-0
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
During the study on the synthesis of straight- and short-chain fatty acids by allylic carbonylation, we used derivatives of acyclic terpenes (III-V) to determine the stereochemistry of the allylic carbonylation. It is shown that the completely different isomer distribution of 4,8-dimethyl-3,7-nonadienoate obtained from the catalytic reaction of the geranyl (III) and neryl (IV) systems indicates that the carbonylation is much faster than the syn-anti isomerization of the pi -allylpalladium complexes, especially in the presence of halide-free palladium catalyst. Namely, the palladium-catalyzed allylic carbonylation occurs before the syn-anti equilibrium is attained; thus it is a kinetically controlled process.
引用
收藏
页码:355 / 358
页数:4
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