Copper-catalyzed oxidative N-S bond formation for the synthesis of N-sulfenylimines
Despite the remarkable success of the copper-catalyzed oxidative coupling reaction, direct cross-coupling of amines and thiols for the synthesis of N-sulfenylimines has not been previously reported. Using commercially available copper catalysts (CuI) and
Lee, Chan,Wang, Xi,Jang, Hye-Young
supporting information
p. 1130 - 1133
(2015/03/14)
A New Synthetic Method for Sulphenimines. Fluoride-catalysed Reaction of N,N-Bis(trimethylsilyl)sulphenamides with Aldehydes and Ketones
A convenient, general method for the preparation of sulphenimines by the reaction of aldehydes and ketones with N,N-bis(trimethylsilyl)sulphenamides in the presence of tetrabutylammonium fluoride catalyst is described.
Thermolysis of α-Azido Sulfides, Sulfoxides, and Sulfones: Dependence of Mechanism on Oxidation State of Sulfur
Thermolyses of α-azidobenzyl phenyl sulfide (1), sulfoxide (3), and sulfone (2) proceed at markedly different rates.Sulfone 2 requires the highest temperature (> 150 deg C), whereas sulfide 1 loses nitrogen at 120 deg C with neighboring group participation by the sulfur atom to produce N-benzylidenebenzenesulfenamide 4 in 75percent yield.Sulfoxide 3 readily decomposes at 70 deg C through a radical-pair intermediate, which gives rise to a CIDNP effect in the reaction products.Kinetic data are presented supporting the suggested reaction mechanisms.
Jarvis, Bruce B.,Nicholas, Paul E.,Midiwo, Jacob O.
p. 3878 - 3882
(2007/10/02)
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