100675-64-7Relevant academic research and scientific papers
Are Radicals Intermediates in Nucleophilic Substitution Reactions of Trityl Halides with Potassium t-Butoxide ?
Hszthy, Peter,Lemport, Karoly,Simig, Gyula,Tamas, Jozsef
, p. 3419 - 3430 (2007/10/02)
The reaction of trityl bromide (2) with potassium t-butoxide in THF furnished in our hands in addition to the substitution products (4) and (10) , compounds (8) and (9) as well as trimeric and oligomeric fractions.The formation of the non-substitution products requires the intermediacy of trityl radicals.Therefore, the suggestion, found in the literature and based solely on the detection of trityl radicals in the reaction mixtures, that substitution products (3) and (4) are formed by the SET mechanism, does not appear to be well founded.
Evidence for Single Electron Transfer in the Reactions of Alkali Metal Amides and Alkoxides with Alkyl Halides and Polynuclear Hydrocarbons
Ashby, E. C.,Goel, A. B.,DePriest, R. N.
, p. 2429 - 2431 (2007/10/02)
Evidence for single electron transfer as the major pathway in reactions previously considered to be classic SN1 and SN2 pathways has been obtained.In this connection, the reaction of KOBu-t with trityl bromide has been shown to proceed through the trityl radical, and the reaction of LiN(i-Pr)2 with a primary alkyl iodide probe gave evidence of proceeding by single electron transfer, as indicated by the cyclized nature of the product as a result of a radical intermediate.
