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.
Wilson, G. Edwin,Hess, Arye
p. 2766 - 2772
(2007/10/02)
More Articles about upstream products of 3075-23-8