343222-47-9Relevant academic research and scientific papers
Azo Anions in Synthesis: α-Amino Carbanion Equivalents from t-Butyldiphenylmethylhydrazones
Baldwin, Jack E.,Adlington, Robert M.,Newington, Ian M.
, p. 176 - 178 (1986)
α-Amino carbanion equivalents (=C(1-)NH2) and α-hydrazino anion equivalents (=C(1-)NHNH2) are readily accessible from the C-alkylation products of t-butyldiphenylmethylhydrazones; these azoalkanes can be efficiently transformed into amines, hydrazines, and also alkanes under mild reaction conditions.
Synthetic applications of α-hydroxydiazenes. III. Uncatalyzed and phenol catalyzed hydroalkylation of alkenes and of azobenzene with alkylazodiphenylmethanols
Yeung, Dominic W. K.,Warkentin, John
, p. 2386 - 2394 (2007/10/02)
Alkylazodiphenylmethanols (C6H5)2C(OH)N=NR, (R = CH(CH3)2, CH2CH3, CH3), when decomposed in the presence of olefinic substrates or in the presence of azobenzene, hydroalkylate those substrates.Addition of R and H across the double bond of an unsymmetric alkene occurs with the regiochemistry expected for a radical mechanism, in which the grooup R adds first.Radical intermediates from decomposition of alkylazodiphenylmethanols have been demonstrated earlier with spin trapping experiments.The fact that addition of phenol can enhance the yield of hydroalkylation product suggests that the process is a radical chain reaction, with chain carrying steps consisting of the reactions: (i) R. + CH2=CHY -> RCH2C.HY (ii) RCH2C.HY + (C6H5)2C(OH)N2R -> RCH2CH2Y + (C6H5)2CO + N2 + R..One deuterioalkylation and some yield-optimizing experiments are also reported.
