Journal of Organic Chemistry p. 3509 - 3514 (1987)
Update date:2022-08-30
Topics:
Lusztyk, J.
Maillard, B.
Deycard, S.
Lindsay, D. A.
Ingold, K. U.
Arrhenius parameters for the reaction of a secondary alkyl radical with tri-n-butylgermanium hydride have been measured by using the cyclization of 1-methyl-5-hexenyl radical as a "clock" reaction.At 298 K the rate constant is 1.8*104 M-1s-1, which makes the secondary alkyl radical/n-Bu3GeH reaction about 80 times slower than the corresponding reaction with tri-n-butyltin hydride.The secondary alkyl radical clock reaction has been rather precisely calibrated by using new data and data from the literature.At attempt to carry out similar experiments with 1,1-dimethyl-5-hexenyl yielded much less precise data for the cyclization o f this tertiary alkyl radical.Reliable kinetic data for hydrogen abstraction from n-Bu3GeH by tertiary alkyl radicals could not be obtained by using either the parent bromide or appropriate N-hydroxypyridine-2-thione esters as alkyl radical sources.
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