The facile desulfation of neutral sulfate ester salts in boiling moist dioxane is well known. The present studies provide evidence that the solvolysis requires initiation by traces of impurities presumably behaving M e1ect.mphiles. The surface of a glass containing vessel is adequate to initiate a reaction which is precipitously catalyzcd to completion by the acidic product's produced. In clean 1'eflon vessels but not in glass, 2-octanol (potassium sulfate) (I) and the cholestan-3&ol analog (11) are stable for prolonged periods in hot moist dioxane, but are almost instantly solvolyeed following addition of almost any trivial potentially acidic contaminant cncountcred in a laboratory environment. At ambient temperature, dioxane solutions-suspensions of I and I1 are solvolyzed in less than 1 hr after addition of a trace of H2SO4 or other electrophilic reagents.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.