Concepedia

Reductive Carbon–Sulfur Bond Cleavage: A Simple Pathway to Nonstabilized (Lithiomethyl)amines

Carsten Strohmann, Bors C. Abele

Angewandte Chemie International Edition in English · 1996 · 37 citations · 21 references

DOI

Concepts

Abstract

Compounds with the structural element -CH2NR2 are easily accessible from (phenylthiomethyl)amines by reductive CS bond cleavage and subsequent addition or substitution (see below). One advantage of this shorter method than tin–lithium exchange is the ready availability of the starting materials, which need not be purified by chromatography.

References

21

Are Polar Organometallic Compounds “Carbanions”? The Gegenion Effect on Structure and Energies of Alkali‐Metal Compounds

Christoph Lambert, Paul von Ragué Schleyer · Angewandte Chemie International Edition in English · 1994 · 218 citations

, , +14

A general preparative method for .alpha.-lithioethers and its application to a concise, practical synthesis of brevicomin

Theodore Cohen, James R. Matz · Journal of the American Chemical Society · 1980 · 172 citations

, , +4

Physical properties and synthetic utility of .alpha.-alkoxyorganolithium species as studied through ligand selectivity in tin-lithium exchange

J. Scott Sawyer, Andrew Kucerovy, Timothy L. Macdonald et al. · Journal of the American Chemical Society · 1988 · 164 citations

, , +10

Two-flask preparation of .alpha.-lithio cyclic ethers from .gamma.- and .delta.-lactones. Reductive lithiation as a route, via radical intermediates, to axial 2-lithiotetrahydropyrans and their equilibration to the equatorial isomers

Theodore Cohen, Ming Teh Lin · Journal of the American Chemical Society · 1984 · 110 citations

, , +6

N,N-Disubstituted aminomethyllithium compounds

Donald J. Peterson · Journal of the American Chemical Society · 1971 · 106 citations

, , +6