Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
The N→O Acetyl Migration of 5-Substituted-2-pyrrolidinemethanols
Hisayuki SakuraiToshiyasu Ishimaru
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1969 Volume 42 Issue 12 Pages 3524-3528

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Abstract

In order to obtain information about the stereochemistry of a fused-ring system, cis and trans isomers of 5-methyl- and 5-phenyl-2-pyrrolidinemethanols were synthesized and rate constants for their N→O acetyl migrations were measured. Each product was a mixture of cis and trans isomers. For both 5-methyl and 5-phenyl derivatives, it was observed that trans isomers migrated faster than cis isomers. The results were discussed in relation to stereochemistry.

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