Journal of the Chemical Society. Perkin transactions II p. 385 - 388 (1985)
Update date:2022-08-04
Topics:
Courtneidge, John L.
Davies, Alwyn G.
When carboxylic acids RCH2CO2H (R = H, Me, Et, or Pr) are photolysed, either neat or in carbon tetrachloride, the e.s.r. spectra of only the radicals RC.HCO2H are observed.Isobutyric acid Me2CHCO2H, similarly shows the spectrum of the radical Me2C.CO2H at room temperature, but at lower temperatures the spectrum of the radical Me2C.H can also be observed.Pivalic acid Me3CCO2H, shows only the spectrum of the Me3C. radical.This is in contrast to the behaviour of the acids in polar solvents, when they normally show Norrish I cleavage of the alkyl-acyl bond, or photoreduction by the solvent.Two models are considered, to account for the regiospecific formation of the radicals RC.HCO2H.The first assumes that cleavage of a C-OH bond in a hydrogen-bonded dimer yields an HO. radical which is hydrogen-bonded to a carbonyl group of the acid
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