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.
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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.