The mechanism of the Cr(VI) oxidation of an alkene C@C is not known for certain. A particularly useful and novel example of this process is the intramolecular oxidative cyclization of bishomoallylic tertiary alcohols by pyridinium chlorochromate (PCC) to yield substituted tetrahydrofuran products via the tethered chromate ester. Several such tertiary alcohols were prepared in this study which varied in the number and position of alkyl groups attached to the C@C. The relative reactivity of these substrates toward PCC under standard conditions is dependent only on the number of R groups on the C@C, not on the degree of substitution on the most highly substituted alkene carbon. This observation suggests a symmetrical transition state in this intramolecular Cr(VI) alkene oxidation.
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