Stereochemistry of the Elimination of Norcamphor‐ and Apocamphor Tosylhydrazone with Methyllithium
作者:
Kwang‐Ting Liu,
Robert H. Shapiro,
期刊:
Journal of the Chinese Chemical Society
(WILEY Available online 1969)
卷期:
Volume 16,
issue 1‐2
页码: 30-36
ISSN:0009-4536
年代: 1969
DOI:10.1002/jccs.196900007
出版商: WILEY‐VCH Verlag
数据来源: WILEY
摘要:
AbstractUpon treatment with three equivalents of methyllithium in ether at room temperatureexo‐3‐d‐norcamphor tosylhydrazone gave norbornene which retained 21% of the deuterium andexo‐3‐d‐apocamphor tosylhydrazone gave apobornylene which retained 50% of the deuterium based on nmr and mass spectral analysis. In both casesexo‐elimination is favored when the primary isotope effect is considered. The relatively low selectivity betweenexo‐andendo‐elimination as compared with that observed in solvolytic studies was tentatively rationalized by the carbarion character of the transition state leading to proton abstra
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