Stereochemistry of the Reactions of Cyclic Ketones with Lithium Aluminum Hydride and Methyllithium. IV. The Stereochemistry of the Reactions in 2,2‐Dimethyl‐4‐t‐Butylcyclohexanone Systems
作者:
Min‐Hon Rei,
C. L. Chen,
H. L. Liu,
期刊:
Journal of the Chinese Chemical Society
(WILEY Available online 1983)
卷期:
Volume 30,
issue 1
页码: 1-9
ISSN:0009-4536
年代: 1983
DOI:10.1002/jccs.198300001
出版商: WILEY‐VCH Verlag
关键词: Stereochemistries;2,2‐Dimethyl‐4‐t‐Butylcyclohexanone Systems
数据来源: WILEY
摘要:
AbstractPrevious publication showed that the stereochemistry of lithium aluminum hydride reduction of cyclic ketones can be evaluated by the use of an empirical equation, . This paper reports further test of this relationship in the new system of 2,2‐dimethyl‐4‐t‐butyl‐cyclohexanone.Lithium aluminum hydride reduction of this ketone yields 95.6%trans‐alcohol (lit., 95.9%) corresponding to D̊(D̊G*)Hof 1.67Kcal/mol. With methyllithium, the ketone formed 77.5% oftrans‐alcohol (D̊(D̊G*)D̊fs= 0.67Kcal/mol). These data give a calculatedD̊G* = 0.74Kcal/molwhich agrees well with the literature value of 0.87 or 0.28Kcal/mol.Structural assignments of 2,2‐dimethyl‐4‐t‐butylyclohexanone, 1,2,2‐trimethyl‐cis‐ andtrans‐4‐t‐butylcyclohexanols by
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