M. Tokuda*, Yoshihiko Watanabe, M. Itoh
Mar 1, 1978
Citations
0
Influential Citations
6
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
Photochemical reaction of ethyl 2-oxo-1-cyclohexanecarboxylate (3) in methanol gave ethyl methyl heptanedioate, trans- and cis-ethyl 7-oxo-2-heptenoate, and ethyl 7-oxo-3-heptenoate in 25, 7, 8, and 21% yields, respectively. Photochemical reactions of 3 in ethanol, isopropyl alcohol, and t-butyl alcohol gave the corresponding ω-alkoxycarbonyl esters. Other 2-(alkoxycarbonyl)-cyclopentanones and -cycloheptanone underwent similar reactions to give the corresponding ω-alkoxycarbonyl esters. Photochemical reactions of 2-cyanocyclohexanones in methanol similarly gave ω-cyano esters and ω-formyl α,β-unsaturated nitriles. However, photochemical reactions of 2-(phenylthio)- and 2-(methylthio)cyclohexanones in methanol did not give the corresponding ω-phenylthio or ω-methylthio carboxylic acid esters, products resulting from a preferential cleavage of a carbon-sulfur bond being obtained.