Bulletin of the Chemical Society of Japan p. 3629 - 3636 (1988)
Update date:2022-08-16
Topics:
Kamimura, Akio
Ono, Noboru
Denitrohydrogenation reaction of aliphatic nitro compounds with tributyltin hydride (Bu3SnH) is accelerated in the presence of radical initiators.ESR and electrochemical measurements reveal that the reductive cleavage of the carbon-nitrogen bond proceeds not via anion radicals of nitro compounds such as SRN1 reaction but via β-scission of (tributylstannyloxy)nitroxyl radicals.The relative reactivities of tin radicals toward substituted α-nitrocumenes, α-nitroethylbenzenes, and α-nitropropiophenones exhibits excellent Hammett correlations with positive ρ values.This tendency has also been found in the reaction of benzyl halides with tin radical.These results suggest that the carbon-nitrogen bond breaking from nitroxyl radical intermediates should take place in rate-determining step for the reaction.
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