(Dialkoxymethyl) lithiums: generation, stability, and synthetic transformations

…, T Tsunoda, BA Goodman, S Ingham…

Index: Shiner, Christopher S.; Tsunoda, Tetsuto; Goodman, Burton A.; Ingham, Stephen; Lee, Shi-hung; Vorndam, Paul E. Journal of the American Chemical Society, 1989 , vol. 111, # 4 p. 1381 - 1392

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Citation Number: 55

Abstract

Abstract:(Dialkoxymethyl) lithium reagents,(RO), CHLi, can be generated simply and efficiently and employed as synthetically useful one-carbon nucleophiles. Reductive lithiation of phenylthio-substituted precursors,(RO), CHSPh, at-95 OC or transmetalation of tri-n-butylstannyl compounds,(R0) 2CHSn (n-Bu) 3, at-1 10 to-1 11 OC afforded the acyclic species (MeO), CHLi (4) and (EtO), CHLi (5). The cyclic reagents, 2-lithio-1, 3-dioxolane (6 ...