100449-39-6Relevant articles and documents
Investigations on 1,3 Thiazines, 35. - Oxidations of Thiocarbamidates, 9. - Unusual Rearrangement Upon Thiocarbamoylation of Tetrahydro-2H-1,3-thiazin-2-one
Hanefeld, Wolfgang,Guenes, Zeynel E.
, p. 1140 - 1146 (2007/10/02)
During thiocarbamoylation of tetrahydro-2H-1,3-thiazin-2-one (4) with N,N-disubstituted thiocarbamoyl chlorides the 3-carboxamides 2 were isolated besides the expected 3-thiocarboxamides 6.The carboxamides 2 are interpreted as products of initial O-thiocarbamoylation, subsequent Newman-Kwart rearrangement, and final S->N-transcarbamoylation.Structures were ensured by independent syntheses and 13C-NMR spectroscopy.Thiocarbamidate and thiourea substructures were converted into the corresponding oxygen analogues by oxidative desulfurisation.