Journal of the American Chemical Society p. 2683 - 2686 (1991)
Update date:2022-08-04
Topics: Substituents Steric Effects Reaction Mechanism Solvent and Reaction Conditions Radical Stability Activation Energy
Hilborn, James W.
Pincock, James A.
Rates of decarboxylation (kCO2R) have been estimated for the acyloxy racicals 7a-f formed in the photolysis of substituted 1-naphthylmethyl 6a-f. These rates are on a mechanism involving initial carbon-oxygen homolytic bond cleavage from the excited singlet state. The products are formed by two competing pathways: electron transfer in the radical pair to give an ion pair and decarboxylation. Measured product yields along with an of the electron-transfer rate (kET) allow calculation of kCO2R as a function of R. The values obtained are the following (R, k (109 s-1)): CH3, < 1.3; CH3CH2, 2.0; (CH3)2CH, 6.5; (CH3)3C, 11; PhCH2, 5.0; PhCH2CH2, 2.3.
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