Abstract
Tetrahedron Letters No.23, pp. 2G03-2006, 1970. Pergamon Press. Printed i n Great Britain. A NOVEL RING CONTRACTION DURING THE VAPOR PHASE PYROLYSIS OF SUBSTITUTED TRANS-1-HYDROXY-2-ACETOXYCYCLOHEXANES John C. Leffingwell and Ronald E. Shackelford (Research and Development Departments, R. J. Reynolds Tobacco Company Winston-Salem, North Carolina 27102) (Received in USA 25 February 1970; r eceived in UK for publi cation 20 April 1970) The vapor phase pyrolysis of a number of terpene hydroxyacetates derived from terpene epoxides has been reported by Royals and Leffingwell to give terpenoid allylic alcohols.1 During a reinvestigation and extension of this earlier work, we have discovered that pyrolytic ring contractions which produce ketonic products accompany the formation of the previously reported allylic alcohols. We have now demonstrated the generality of such pyrolytic ring contractions by the pyrolysis of five substituted trans-1-hydroxy-2-acetoxycyclohexanes. On pyrolysis these systems all follow the general equation:
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