Abstract Tertiary alcohols 5 and 8 undergo rearrangement on treatment with thionyl chloride and pyridine, yielding octahydronaphthalenes 6 and 9, respectively. Alcohol 12 under similar treatment affords a mixture of tetrahydronaphthalene 14 and diene 15, whereas alcohol 22 suffers no rearrangement but produces olefin 23.
