114234-22-9Relevant academic research and scientific papers
Radical Cyclizations of Alkenyl-Substituted 4,5-Dihydro-1,3-thiazole-5-thiols
Jenny, Christjohannes von,Wipf, Peter,Heimgartner, Heinz
, p. 838 - 846 (2007/10/02)
Heating of 5-alkenyl- or 5-alkinyl-4,5-dihydro-1,3-thiazole-5-thiols of type 5 in the presence of a radical initiator gave dithiaspirobicycles in fair-to-excellent yield (Scheme 3).Under analogous conditions, the 4,5-dihydro-4-vinyl-1,3-thiazole-5-thiol 5d underwent a cyclization to give the annellated dithiabicycle 7 (Scheme 4).In this reaction, a minor product 8 was formed by an unknown reaction mechanism.The structure of 8 was established by X-ray crystallography.The starting 1,3-thiazole-5-thiols 5 have been synthesized by carbophilic alkylation of the C=S group of 1,3-thiazole-5(4H)-thiones with Grignard-reagents or alkylcuprates.The thiazolethiones were obtained by the reaction of 3-amino-2H-azirines with thiobenzoic acid followed by sulfurization and cyclization.The 4-benzyl derivative 1b was thermally rearranged via 1,3-benzyl migration to yield the benzyl (1,3-thiazol-5-yl) sulfide 11 (Scheme 5).
2,4-Bis(4-methylphenylthio)-1,3,2λ5,4λ5-dithiadiphosphetane-2,4-dithione: A New Reagent for Thiation of N,N-Disubstituted Amides
Wipf, Peter,Jenny, Christjohannes,Heimgartner, Heinz
, p. 1001 - 1011 (2007/10/02)
As a new reagent for the thiation of amides, the easily accessible 2,4-bis(4-methylphenylthio)-1,3,2λ5,4λ5-dithiadiphosphetane-2,4-dithione (9) shows a remarkable selectivity.This selectivity - the preferred thiation of N,N-disubstituted amides - is complementary to the one of the well known Lawesson reagent.Thiation of diamides of type 2 with 9 leads via cyclization of the corresponding dithiodiamides directly to 1,3-thiazole-5(4H)-thiones 1.
