Jump to main content
Jump to site search
Access to RSC content Close the message box

Continue to access RSC content when you are not at your institution. Follow our step-by-step guide.


Issue 6, 1973
Previous Article Next Article

The mechanism of the rearrangement of β-acyloxyalkyl radicals

Abstract

Determination of the distribution of products from decarbonylation of 2-formyl-1,1-dimethylethyl heptanoate (6d) and other esters of 3-hydroxy-3-methylbutanal, and from the reaction of tributylstannane with 2-bromo-1,1-dimethylethyl benzoate (11b), 2-bromo-1-methyl-1-phenylethyl acetate (11c), and similar bromo-esters, has enabled the rates of rearrangement of some β-acyloxyalkyl radicals to be evaluated. The kinetic data together with the results of reactions using 18O labelled substrates indicate that 1,2-acyloxy-transfer proceeds via a concerted mechanism involving a five-membered cyclic transition state. The rate of rearrangement of the 2-acetoxy-2-phenylpropyl radical (12c) by 1,2-aryl migration has also been determined.

Back to tab navigation

Article information


J. Chem. Soc., Perkin Trans. 2, 1973, 861-872
Article type
Paper

The mechanism of the rearrangement of β-acyloxyalkyl radicals

A. L. J. Beckwith and C. B. Thomas, J. Chem. Soc., Perkin Trans. 2, 1973, 861
DOI: 10.1039/P29730000861

Search articles by author

Spotlight

Advertisements