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1-Haloethynyl-2-methylcyclopentanols treated with iodine and HTIB ring expand stereoselectively depending on the relative position of the methyl and the hydroxyl groups. The products are 2-(dihalomethylidene)-3-methylcyclohexanones if the methyls are cis to the hydroxyl groups or 2-(dihalomethylidene)-6-methylcyclohexanones if the methyls are trans to the hydroxyls.
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Herault et al. (1996) studied this question.
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