Further evidence to understand the stereochemistry of the reactions of α‐sulfinyl carbanions
作者:
Atsuyoshi Ohno,
Masato Higaki,
Mutsuo Okamura,
期刊:
Heteroatom Chemistry
(WILEY Available online 1992)
卷期:
Volume 3,
issue 5‐6
页码: 513-519
ISSN:1042-7163
年代: 1992
DOI:10.1002/hc.520030511
出版商: VCH Publishers, Inc.
数据来源: WILEY
摘要:
AbstractThe stereochemistry of the α‐sulfinyl carbanion has been studied. It has been elucidated that a 2‐pyridylmethyl substituent on the sulfinyl sulfur chelates onto the counter cation in an ion pair to fix the conformation of the anion at a particular orientation. Then, the steric bulk of the other substituent plays a role to control the reacting face. A soft electrophile such as methyl iodide attacks the anion from the more open side. On the other hand, a hard electrophile such as a proton is initially trapped by the polar part of the ion pair and no steric effect oper
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