158554-94-0

Upstream product

• 158554-91-7 (S)-3,4-dibenzylthiazolidine-2-thione 

Downstream Products

• 300-57-2 allylbenzene 
• 1826-11-5 2-phenylthiazole 
• 103-29-7 1,1'-(1,2-ethanediyl)bisbenzene 
• 3173-56-6 benzyl isothiocyanate 
• 158554-97-3 (4S)-4-benzyl-2-phenyl-4,5-dihydro-1,3-thiazole 
• 1466-67-7 1,3-dibenzylurea 
• 100-47-0 benzonitrile 
• 108-88-3 toluene 

Relevant academic research and scientific papers

Effect of added benzoic acid on the phase-transfer catalysed permanganate oxidation of organosulfur compounds

The addition of benzoic acid in the oxidation of a range of sulfides and thiazolidinethiones using KMnO4 under phase-transfer conditions provides a convenient and high yielding procedure for formation of the corresponding sulfones, thiazolidinones and thiazolidinone S,S-dioxides.

Synthesis and pyrolytic behaviour of thiazolidin-2-one 1,1-dioxides

Four examples of the chiral thiazolidin-2-one 1,1-dioxides 5 have been prepared by reaction of the appropriate amino alcohols 11 with CS2 in aqueous sodium hydroxide to give the thiazolidine-2-thiones 12, followed by oxidation with KMnO4 under phase-transfer conditions in the presence of benzoic acid, either directly or via the thiazolidin-2-ones 13. Upon flash vacuum pyrolysis (FVP) at 650°C, 5a-c decompose mainly by loss of SO2 to give an alkene and benzyl isocyanate together with other products from fragmentation of the N-benzyl group. A significant minor pathway involves net loss of CO2 and water to give the 2-phenyl-4,5-dihydrothiazoles 21 together with their aromatisation products 22 and 23. A mechanism for this new heterocyclic transformation is proposed involving initial expansion to a cyclic carbamic-sulnnic anhydride (2,1,4-oxathiazin-3-one 1-oxide). The fully assigned 13C NMR spectra are presented for 5, 12 and 13 and the 33S NMR spectrum has been obtained for 5c.

Unexpected Thermal Extrusion of CO2 from 3-Benzylthiazolidin-2-one 1,1-Dioxides to Give 2-Phenylthiazolines and Thiazoles

Flash vacuum pyrolysis of a series of chiral 3-benzylthiazolidin-2-one 1,1-dioxides 5, readily prepared from amino acids, results mainly in loss of SO2 to give an alkene and benzyl isocyanate, but a significant minor pathway involves unexpected loss of CO2 and water to give 2-phenylthiazolines 13 and derived thiazoles.