Paper
The Photo-induced Addition of Acetic Acid to Cyclohexene Derivatives
Published Feb 1, 1973 · T. Leong, T. Imagawa, K. Kimoto
Bulletin of the Chemical Society of Japan
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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.
Acetic acid photo-induced addition to cyclohexene derivatives produces methyl trans-4-acetoxycyclohexanecarboxylate, with benzene as a sensitizer, and two equatorially-substituted acetic-acid a
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