Aqueous chlorination of α-terpineol

Herbert L. Kopperman, Richard C. Hallcher, Agatha Riehl, Robert M Carlson, Ronald Caple

Research output: Contribution to journalArticlepeer-review

27 Scopus citations

Abstract

Of the multitude of products obtained upon the aqueous chlorination of α-terpineol (1), under both acidic and basic conditions, the major ones are the diequatorial trans, 4, and diaxial trans, 5, Markovnikov adducts of hypochlorous acid to the olefinic center. With the exclusion of small amounts of dichloride formation, the remainder of the products appear to be derived from 4 and 5 by hydrolysis or elimination sequences. The product distribution exhibits an expected pH dependence that is useful in the structural assignments.

Original languageEnglish (US)
Pages (from-to)1621-1626
Number of pages6
JournalTetrahedron
Volume32
Issue number14
DOIs
StatePublished - 1976

Bibliographical note

Funding Information:
Acknowledgemenfs-Wea re indebtedt o the EnvironmentaPl ro-tection Agency, Grant No. I8050H IK, for support of this work. We further wish to thank Mr. Douglas Kuebl, National Water Quality Laboratory, Duluth, for his help in obtaininga nd inter-pretingt hem asss pectra.W e also wish to thankG erard Putz, John D. Nelson, Kathleen Mielke, and Robert J. Schmitt for their technicala ssistance.

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