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Abstract
Dialkylaluminum chloride (R2A1C1) catalyzed ene reactions of carbonysulfide (OCS) as an enophile with alkenes were performed. R2A1C1 selectively complexed to the thionyl sulfur of OCS, then reacted with different alkenes and formed the corresponding β,γ -unsaturated thioic acid ene adducts. Those alkenes were limonene (1), β-pinene (2) and methylenecyclohexane (3). The reaction with limonene (1) gave 4-methyl- β -methylene-3-cyclohexene-1-propanethioic acid (4). From β-pinene (2) was obtained 6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-ethanethioic acid (5) while methylenecyclohexane (3) afforded 1-cyclohexene-1-ethanethioic acid (6).