Preparative Organic Chemistry
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ChemInform Abstract: The Allylic Rearrangement. Part 5. Reaction of 4-Haloisophorone with Sodium Methoxide in Methanol.
First published: January 26, 1988
Abstract
Isophorone (I) is converted to the chloro and bromo derivatives (III) by treatment with the N-halosuccinimides (II).
ChemInform Abstract
Isophorone (I) is converted to the chloro and bromo derivatives (III) by treatment with the N-halosuccinimides (II). Reaction of the chloride (IIIa) with sodium methoxide (IV) gives the methoxyisophorone (V) and the unsaturated 5-ring carboxylates (VI) and (VII). The product ratio depends on the temperature and the amount of methoxide used. The structure of the isomers (VI) and (VII) is established by catalytic hydrogenation, yielding the cyclopentanecarboxylate (VIII). Treatment of the bromoisophorone (IIIb) with sodium methoxide (IV) only produces the methoxy derivative (V).
