52146-63-1

Upstream product

• 2862-88-6 2,2-diphenylthiirane 
• 23695-65-0 adamantane-2-thione 
• 622-79-7 benzyl azide 
• 1450-31-3 Thiobenzophenon 
• 622-37-7 Phenyl azide 
• 830-72-8 9H-fluorene-9-thione 
• 624-49-7 dimethylfumarate 
• 764-42-1 1,2-Dicyanoethylene 
• 52533-09-2 5-(4-methoxyphenyl)-[1,3,4]oxathiazol-2-one 
• 17452-80-1 HT₁₀₄₁ 
• 4214-38-4 (diphenylmethylene)triphenylphosphorane 

Relevant academic research and scientific papers

An efficient synthesis of 1,2-dithiolanes and 1,2,4-trithiolanes by the reaction of phosphorus ylides with elemental sulfur

Reaction of diarylmethylenetriphenylphosphoranes with elemental sulfur followed by the addition of maleic anhydride afforded 1,2-dithiolanes in good yields. When the reaction was carried out in the presence of adamantane-2-thione, two types of 1,2,4-trithiolane were formed. Thiation of thiobenzophenones with elemental sulfur also afforded the corresponding 1,2-dithiolanes.

111. Three-component reactions with sterically crowded 2,2,4,4-tetramethyl-3-thioxocyclobutanone, phenyl azide, and electron-deficient C,C-Dipolarophiles

In order to trap 'thiocarbonyl-aminides' A, formed as intermediates in the reaction of thiocarbonyl compounds with phenyl azide, a mixture of 2,2,4,4-tetramethyl-3-thioxocyclobutanone (1), phenyl azide, and fumarodinitrile (8) was heated to 80° until evolution of N2 ceased. Two interception products of the 'thiocarbonylaminide' A (Ar = Ph) were formed: the known 1,4,2-dithiazolidine 3 (cf. Scheme 1) and the new 1,2-thiazolidine 12 (Scheme 2). The structure of the latter was established by X-ray crystallography (Fig. 1). The analogous 'three-component reaction' with dimethyl fumarate (9) yielded, instead of 8, in addition to the known interception products 3 and 6 (Scheme 1), two unexpected products 15 and 16 (Scheme 3), of which the structures were elucidated by X-ray crystallography (Fig. 2). Their formation is rationalized by a primary [2 + 3] cycloaddition of diazo compound 18 with 1 to give 19, followed by a cascade of further reactions (Scheme 4).

Cascade reaction in a three-component system including adamantanethione, phenyl azide, and dimethyl fumarate

The major product of the three-component reaction with adamantanethione (1), dimethyl fumarate (6), and phenyl azide at 80°C has been determined as the 1-azabuta-1,3-diene derivative 7 by X-ray crystallography. A similar amount of the symmetric dispiro-1,2,4-trithiolane 8 was also found in the reaction mixture. The reaction with N-phenyl maleinimide instead of the fumarate, yielded the known 4,5-dihydro-1,2,3-triazole derivative 9, and the three-component system with 1,3-thiazole-5(4H)-thione 10, dimethyl fumarate (6), and phenyl azide gave a mixture of imine 11, 4,5-dihydro-1,2,3-triazole-4,5-dicarboxylate 12 and the diazo compound 13. A mechanism via a cascade of reactions is proposed to rationalize the formation of 7.

Sulfur centered 1,3-dipoles. An efficient trapping of adamantanethione-S-sulfide generated in the reaction of adamantanethione with organic azides

The reaction of adamantanethione (1) and an organic azide at 80°C ("two-component reaction") yields the symmetrical 1,2,4-trithiolane 9 and the corresponding adamantylidene imine 10 in nearly equal amounts. Under the same conditions, the "three-component reaction" with 1, phenyl azide and an aromatic thioketone gives the unsymmetrical 1,2,4-trithiolane 12 as the major product, and 9 and imine 13 as by-products. A 1,3-dipolar cycloaddition of an intermediate thiocarbonyl-S-sulfide and a thioketone is proposed as the mechanism for the formation of the trithiolanes. The structure of trithiolane 12a has been established by X-ray crystallography.

Dithiazoles and Related Compounds. Part 3. Preparation of 5H-1,4,2-Dithiazoles via 1,3-Dipolar Cycloadditions between Nitrile Sulphides and Thiocarbonyl Compounds, and some Conversions into 3,5-Diaryl-1,4,2-dithiazolium Salts

Thermolysis of 1,3,4-oxathiazol-2-ones 3 in the presence of thiocarbonyl compounds gives modest to good yields of the little-known 5H-1,4,2-dithiazoles 1, the reaction being successful with diaryl, aryl alkyl and dialkyl ketones, and thiono esters, but failing with dithio esters and tertiary thioamides.The influence of substituents is discussed.Solvolysis of 5-ethoxy-5H-1,4,2-dithiazoles, derived from thiono esters, with perchloric acid in acetic anhydride gives high yields of 3,5-diaryl-1,4,2-dithiazolium salts 9.