71687-33-7Relevant academic research and scientific papers
Acylations of Thiol Ester Enolate Anions
Wilson, G. Edwin,Hess, Arye
, p. 2766 - 2772 (1980)
The synthetic utility of thiol ester anions has been explored.Claisen condensations of thiol esters with isopropylmagnesium bromide base proceed in good yield.The Dieckmann reaction of diethyl thiolpimelate to form a six-membered ring proceeds in 74 percent yield, but the corresponding reaction of diethyl thioladipate to provide a five-membered ring gives only 26 percent yield.Neither alkylation of ethyl thiolacetate nor a Michael-type adduct with methyl vinyl ketone could be achieved.The mechanism of the Claisen condensation as it applies to thiol esters is discussed.
