Heterolytic Cleavage of a β-Phosphatoxyalkyl Radical Resulting in Phosphate Migration or Radical Cation Formation as a Function of Solvent Polarity
- 24 May 1999
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 1 (1) , 153-156
- https://doi.org/10.1021/ol990054h
Abstract
The 2-(diethylphosphatoxy)-2-(p-methoxyphenyl)-1,1-dimethylethyl radical (1) reacted to give the benzylic radical product from phosphate migration or a radical cation (or a mixture of the two) as a function of solvent. Smooth acceleration in rates of reactions of 1 in solvents of increasing polarity and consistent entropies of activation indicate that radical 1 reacts by common mechanism irrespective of the final products formed, specifically by initial heterolysis to a radical cation−phosphate anion pair.Keywords
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