Abstract
The anion generated from the isopropyl thioester of (methylenecyclopropyl)acetic acid may be quenched with water to give an unrearranged thioester and an acyclic isomer, isopropyl 4-methylpenta-2 E,4-dienethioate; the coenzyme A thioester of (methylenecyclopropyl)acetic acid is a known inactivator of acyl dehydrogenases. The isopropyl thioester of β-(cyclopropylidene) propionic acid reacts with LDA followed by water to give only 3-(cyclopropyl)prop-2 E-enethioate, and its coenzyme A thioester does not inactivate the acyl dehydrogenase from pig kidney (EC 1.3.99.3).
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