91077-15-5Relevant articles and documents
Conversion of 2-Sulfinylated 2-Alkenoate Esters to (2E,4E)-2,4-Alkadienoate Esters by Pyrolysis
Tanikaga, Rikuhei,Nozaki, Yoshihito,Nishida, Masaharu,Kaji, Aritsune
, p. 729 - 733 (2007/10/02)
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-alkanedioates 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 sigmatropic rearrangement to benzenesulfenate esters, followed by thermolytic extrusion of a benzenesulfenic acid probably via ethyl(2E)-4-phenylsulfinyl-2-alkenoates to afford ethyl (2E,4E)-2,4-alkadienoates.