tert-Butylation of. alpha.,. beta.-Unsaturated Nitriles by tert-Butylmercury Halides in the Presence of Iodide Ion

GA Russell, P Chen, CF Yao…

Index: Russell, Glen A.; Chen, Ping; Yao; Kim Journal of the American Chemical Society, 1995 , vol. 117, # 22 p. 5967 - 5972

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Citation Number: 14

Abstract

Abstract: Iodide ion promotes the free radical addition of t-BuHgI to acrylonitrile to form t- BuCH? CH (CN) HgI. A facile reaction of the adduct 1-cyanoalkyl radical with t-BuHgIz-is indicated. Further promotion is observed in the presence of NI&I or PTSA/KI in a reaction now leading directly to t-BuCH2CH2CN. Protonation of the intermediate adduct radical followed by electron transfer from t-BuHgI2-is postulated. With fumaronitrile reaction of the ...