Abstract
Ethyl and methyl sorbate react with thiols in the corresponding alcohol as solvent and with sodium alkoxide as catalyst. Nucleophilic attack by alkylthiols leads to the formation of diadducts (2,3- and 4,5-addition of H + RS −) whilst reaction with mercaptoethanol, esters of 2-mercaptoacetic acid, and cysteine ethyl ester gives the 2,5-addition product. Detailed consideration is given to the location of the double bond in position 3. Attempted hydrolysis of the esters causes dissociation of monoadducts liberating sorbic acid. However, if sorbic acid is allowed to react with cysteine in a predominantly aqueous medium, and the product esterified, it is identical to that formed from the esters of sorbic acid and of cysteine.
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