Journal of the Chemical Society. Perkin transactions II p. 161 - 166 (1981)
Update date:2022-08-11
Topics:
Baban, Jehan A.
Roberts, Brian P.
The irreversible addition of alkyl radicals to diethyl vinylphosphonate to give the α-phosphorylalkyl radicals (1) has been studied by e.s.r. spectroscopy at 233 K in hydrocarbon solvents.The rate constants for addition (kadd) have been determined relative to those (2kAt) for self-reaction of (1) for a series of addenda.The values of 2kAt have been measured in separate kinetic e.s.r. experiments for (1; R = Me) (2.0 x 1E9 dm3mol-1s-1) and (1; R = But) (5.0 x 1E8 dm3mol-1s-1) and thus absolute values of kadd were obtained.The rate constant kadd increases along the series R. = Me. (2.5 x 1E3 dm3mol-1s-1 ) < Rprim. < Rsec. < But. (5.9 x 1E4 dm3mol-1s-1) and this order is interpreted in terms of the over-riding importance of polar effects in determining the size of the barrier for addition of these nucleophilic radicals to the electron deficient alkene.R. + H2C=CHP(O)(OEt)2 --> RCH2C.HP(O)(OEt)2 (1)
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