T. Leong, T. Imagawa, K. Kimoto
Feb 1, 1973
Citations
0
Influential Citations
3
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
The irradiation of methyl 3-cyclohexene-1-carboxylate in acetic acid in the presence of benzene as a sensitizer yields methyl trans-4-acetoxycyclohexanecarboxylate predominantly, together with a small amount of methyl trans-3-acetoxycyclohexane-1-carboxylate; the corresponding cis-isomers are not detected. Under the same conditions, on the irradiation of dimethyl esters of cis- and trans-4-cyclohexene-1,2-dicarboxylic acids, the two possible isomers of acetic-acid adducts with respect to each starting substance are obtained. The irradiation of trans-8-oxabicyclo[4.3.0]non-3-ene gives the two possible acetic-acid adducts, whereas in the case of the irradiation of the cis-isomer, only two equatorially-substituted acetic-acid adducts are obtained. The structural elucidation and the mechanism of the formation of these compounds are discussed.