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1973•Canadian Journal of ChemistryRequires access

Steric Effects in the Baeyer–Villiger Reaction of Simple Ketones

Mitchell A. Winnik, Valerie Stoute

Open publisher page 21 citations

Abstract

The reactions of simple alkyl ketones with peroxytrifluoroacetic acid (PTFA) and peroxymaleic acid (PMA) have been examined. Magnitudes of steric effects in the Baeyer–Villiger reaction have been determined, the largest being a factor of 13 in neopentyl to ethyl migration in 5,5-dimethyl-3-hexanone. PMA is consistently more selective toward electronic differences in migrating groups. PTFA shows the greater sensitivity to steric effects.

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What this paper is about

The reactions of simple alkyl ketones with peroxytrifluoroacetic acid (PTFA) and peroxymaleic acid (PMA) have been examined. Magnitudes of steric effects in the Baeyer–Villiger reaction have been determined, the largest being a factor of 13 in neopentyl to ethyl migration in 5,5-dimethyl-3-hexanone. PMA is consistently more selective toward electronic differences in migrating groups. PTFA shows the greater sensitivity to steric effects.

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Available abstract

The reactions of simple alkyl ketones with peroxytrifluoroacetic acid (PTFA) and peroxymaleic acid (PMA) have been examined. Magnitudes of steric effects in the Baeyer–Villiger reaction have been determined, the largest being a factor of 13 in neopentyl to ethyl migration in 5,5-dimethyl-3-hexanone. PMA is consistently more selective toward electronic differences in migrating groups. PTFA shows the greater sensitivity to steric effects.

Key concepts: Steric effects, Chemistry, Steric factor, Alkyl, Electronic effect, Organic chemistry, Ketone, Medicinal chemistry

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