Abstract
The reaction between 2,3-epoxy-2-methylpentane and mercaptoacetic acid yields a 3:4 mixture of the thialactone ( 2a ) and the hydroxyacetate ( 3b ). Using milder reaction conditions, only the mercaptoester ( 3a ) is formed, which has been shown to be an intermediate in the formation of the acetate ( 3b ). The reactivity of mercaptoacetic acid towards the epoxide is not due solely to the action of the mercapto or carboxylic acid group and therefore may result from the formation of cyclic intermediates.
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