REACTION OF 2-(1,3-BUTADIENYL)MAGNESIUM CHLORIDE WITH CARBONYL-COMPOUNDS AND EPOXIDES - REGIOSELECTIVITY STUDY

被引：84

作者：

NUNOMOTO, S ^{[1
]}

YAMASHITA, Y ^{[1
]}

机构：

[1] NAGOYA UNIV,FAC ENGN,DEPT SYNTHET CHEM,NAGOYA,AICHI 464,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1979年 / 44卷 / 26期

关键词：

D O I：

10.1021/jo00394a009

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of 2-(1, 3-butadienyl)magnesium chloride (1) with carbonyl compounds and epoxides afforded a mixture of the “normal” addition product 1, 3-dienyl alcohol and the “rearranged” allenic alcohol. The formation of the “rearranged” allenic alcohol was favored by lower basicity of solvent, by more covalent carbon-metal bonding, and by increased steric hindrance in ketones. The regioselectivity of the reaction was consistent with the six-membered cyclic transition state 10. © 1979, American Chemical Society. All rights reserved.

引用

页码：4788 / 4791

页数：4

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