Abstract
The behaviour in acid media of hydroxy selenides and hydroxy sulfides ( 1a-c and 1′a-c) was investigated. The protection of the primary hydroxyl group in compounds 1a and 1′a allowed the stereoselective synthesis of a substituted tetrahydrofuran ring, whereas compounds 1b-c and 1′b-c gave an efficient regiochemical control affording substituted tetrahydropyran rings. Tetrahydropyrans containing the phenylselanyl moiety were found to be in equilibrium in the cyclization reaction conditions, whereas tetrahydropyrans containing the phenylsulfanyl moiety were not. A mechanism for the above equilibration is proposed. Semiempirical (AM1, PM3) and ab initio (HF/3-21G ∗) calculations were used in an attempt to rationalize the experimental results.
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