The lead tetraacetate reaction of alcohols containing a small ring. Part II. Cyclobutane‐methanols and cyclopropane‐ethanols

Abstract

The leadtetraacetate and lead tetraacetate/metal chloride oxidations of cyclobutane‐methanol, cyclopropane‐ethanol and the corresponding α, α‐diniethyl alcohols have been investigated and compared with the oxidative reactions of cyclobutane‐carboxylic acid, cyclopropane‐acetic acid and 4‐pentenoic acid, performed with the same reagents and under similar conditions. It was found that alcohol β‐fragmentation and acid decarboxylation follow a remarkably similar mechanistic course, affording comparable results when the substrates are of the same structural type (1, 2 and 5; 3, 4 and 6) or are converted to the same intermediate alkyl radical fragments (3, 4, 6 and 7). In addition, cyclization products formed from cyclopropane‐ethanol (dihydropyran derivative 31) and 4‐penteuoic acid (γ‐lactones 38) have been isolated and identified.