Aminomethylation of Thioureas with N,N-Dimethyl-1-(triethylsiloxy)methanamine, Involving Amino Group Exchange


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Abstract

The O-triethylsilylated hemiaminal Et3SiOCH2NMe2 readily transfers the Me2NCH2-group to various thioureas under mild conditions and without catalysts or co-reagents. In the reaction with PhNHC(=S)·NHPh, the initially formed mono-substituted derivative PhNHC(=S)NPhCH2NMe2 readily rearranges to produce the unsymmetrical thiourea PhNHC(=S)NMe2 and hexahydro-1,3,5-triphenyl-1,3,5-triazine.

About the authors

J. McMahon

Department of Chemistry

Email: kpannell@utep.edu
United States, El Paso, Texas, 79968

H. K. Sharma

Department of Chemistry

Email: kpannell@utep.edu
United States, El Paso, Texas, 79968

A. Metta-Magaña

Department of Chemistry

Email: kpannell@utep.edu
United States, El Paso, Texas, 79968

K. H. Pannell

Department of Chemistry

Author for correspondence.
Email: kpannell@utep.edu
United States, El Paso, Texas, 79968

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