R. Tanikaga, Y. Nozaki, M. Nishida
Mar 1, 1984
Citations
0
Influential Citations
19
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
Thermal reaction of ethyl (2E)-2-phenylsulfinyl-2-alkenoates (E-2) prepared from aldehydes and ethyl 2-phenylsulfinylacetate have been investigated. Refluxing of E-2 or their Z-isomers in xylene resulted in the formation of ethyl (2E,4E)-2,4-alkadienoates accompanied by ethyl (2E)-4-hydroxy-2-alkenoates. Ethyl 2-cycloalkylidene-2-phenylsulfinylacetates were found to be more susceptible to pyrolysis. The enoate esters (2) undergo migration of their carbon-carbon double bond and then [2,3]sigmatropic rearrangement to benzene-sulfenate esters, followed by thermolytic extrusion of a benzenesulfenic acid probably via ethyl (2E)-4-phenyl-sulfinyl-2-alkenoates to afford ethyl (2E,4E)-2,4-alkadienoates.