Abstract
Abstract The aluminum chloride-catalyzed reactions of cis-Δ4-tetrariydrophthalic acid (1A) and its dimethyl ester (3A) with benzene gave, stereoselectively, t-4-phenyl-cis-bexahydrophthalic acid (2A) and its dimethyl ester (12) respectively. Similarly, the reactions of trans-Δ4-tetrahydrophthalic acid (1B) and its dimethyl ester (3B) with benzene gave, stereoselectively, c-4-phenyWrtrans-hexahydrophthalic acid (2B) and its dimethyl ester respectively, accompanied by a small amount of the c-4,t-2,r-1-isomer. The mechanism can be explained by presuming the interaction of the lone-pair electrons of carbonyl oxygen in the axial carboxyl group with a vacant p-orbital of the carbonium ion, which is produced by protonation to the double bond of the cyclohexenes (1A, 1B, 3A, 3B).
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