Reactions of Lithio Trimethylsilyl Compounds with Nitrones

Article abstract of DOI:10.1021/jo00147a026

The reactions of lithio compounds, generated in situ from 2-<(trimethylsilyl)methyl>pyridine (1), N,N-dimethyl(trimethylsilyl)acetamide (2), and ethyl (trimethylsilyl)acetate (3) and LDA in THF, with various nitrones have been investigated.The lithio compounds of 1-3 reacted with α,N-diarylnitrones to give the corresponding (E)-alkenes together with azoxybenzene and/or azobenzene.On the other hand, the reaction of lithio derivative of 1 with α-aryl-N-alkylnitrones, α,N-dialkylnitrones, and cyclic nitrones afforded the aziridine compounds as the major products, accompanied by hydroxylamine derivatives in some cases.The lithio derivative of 2 or 3 reacted with α,N-dialkylnitrones and cyclic nitrones to give the aziridine and/or isoxazolidinone derivatives.The pathways for the formation of the above products are also described.