52146-63-1

Basic information

• Product Name: dispiro[adamantane-2,3'-[1,2,4]-trithiolane-5',2''-adamantane]
• Synonyms: dispiro[adamantane-2,3'-[1,2,4]-trithiolane-5',2''-adamantane]
• CAS NO: 52146-63-1
• Molecular Formula: C₂₀H₂₈S₃
• Molecular Weight: 364.63132
• Mol File: 52146-63-1.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: dispiro[adamantane-2,3'-[1,2,4]-trithiolane-5',2''-adamantane](CAS DataBase Reference)
• NIST Chemistry Reference: dispiro[adamantane-2,3'-[1,2,4]-trithiolane-5',2''-adamantane](52146-63-1)
• EPA Substance Registry System: dispiro[adamantane-2,3'-[1,2,4]-trithiolane-5',2''-adamantane](52146-63-1)

Safety Data

• Hazardous Substances Data: 52146-63-1(Hazardous Substances Data)

Upstream product

• 23695-65-0 adamantane-2-thione 
• 622-79-7 benzyl azide 
• 1450-31-3 Thiobenzophenon 
• 622-37-7 Phenyl azide 
• 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 
• 830-72-8 9H-fluorene-9-thione 
• 2862-88-6 2,2-diphenylthiirane 

Relevant articles and documents

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.

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.