Chemistry Letters
Online ISSN : 1348-0715
Print ISSN : 0366-7022
ISSN-L : 0366-7022
BASE-CATALYZED SKELETAL ISOMERIZATION OF 6-ENDO-HYDROXY-9-THIABICYCLO[3.3.1]NONA-3,7-DIEN-2-ONE WITH THE EPIMERIZATION OF THE HYDROXY GROUP
Tsutomu MiyashiNobukazu SutoToshio Mukai
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1978 Volume 7 Issue 2 Pages 157-160

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Abstract

Studies on the base-catalyzed skeletal isomerizatici of (4) to (5) and (6) and the base-catalyzed epimerization of the hydroxy group in (5) and (6) are reported. The most plausible mechanism for the skeletal isomerization of (4) and the epimerization in (5) and (6) involves retro-aldol cleavages of (4), (5) and (6) to give an enolate (7) as the common intermediate.

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