ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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.
Additional Material:
3 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19760590214
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