300539-09-7

Basic information

• Product Name: 1,2,4-Trithiolane, 3,5-bis(1,1-dimethylethyl)-3,5-diphenyl-, (3R,5S)-rel-
• CAS NO: 300539-09-7
• Molecular Formula: C22H28S3
• Molecular Weight: 388.662
• Mol File: 300539-09-7.mol

Chemical Properties

• CAS DataBase Reference: 1,2,4-Trithiolane, 3,5-bis(1,1-dimethylethyl)-3,5-diphenyl-, (3R,5S)-rel-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,4-Trithiolane, 3,5-bis(1,1-dimethylethyl)-3,5-diphenyl-, (3R,5S)-rel-(300539-09-7)
• EPA Substance Registry System: 1,2,4-Trithiolane, 3,5-bis(1,1-dimethylethyl)-3,5-diphenyl-, (3R,5S)-rel-(300539-09-7)

Safety Data

• Hazardous Substances Data: 300539-09-7(Hazardous Substances Data)

Upstream product

• 938-16-9 2,2-dimethylpropiophenone 
• 40920-09-0 tert-butyl phenyl thioketone 
• 187847-76-3 6-tert-butyl-6-phenylpentathiane 

Downstream Products

• 40920-09-0 tert-butyl phenyl thioketone 

Relevant articles and documents

Oxidation of cis- and trans-3,5-Di-tert-butyl-3,5-diphenyl-1,2,4-trithiolanes: Isolation and Properties of the 1-Oxides and the 1,2-Dioxides

Oxidation of trans-3,5-di-tert-butyl-3,5-diphenyl-1,2,4-trithiolane with dimethyldioxirane (DMD) or m-chloroperbenzoic acid (MCPBA) gave two stereoisomeric (1S*,3S*,5S*) - and (1R*,3S* ,5S*)-1-oxides (16 and 17, respectively). Oxidation of 16 with DMD gave the (1S*,2R*,3S*,5S*)-1,2-dioxide (18) and the 1,1-dioxide 19, and that of 17 yielded the (1R*,2R*,3S* ,5S*)-1,2-dioxide (20) mainly along with 18 and 19. The structures of the 1,2-dioxides 18 and 20 were determined by X-ray crystallography. 1,2-Dioxides 18 and 20 isomerized to each other in solution, and the equilibrium constant K (20/18) is 19 in CDCl3 at 295 K. The kinetic study suggested a biradical mechanism for the isomerization. Isomerization of 16 and 17 to cis-3,5-di-tert-butyl-1,2,4-trithiolane 1-oxides by treatment with Me 3O+BF4- is also described.

Structure elucidation of 6-t-butyl-6-phenylpentathiane monoxides by X-ray crystallography and DFT calculations

6-t-Butyl-6-phenylpentathiane was oxidized with trifluoroperacetic acid (CF3CO3H) or dimethyldioxirane (DMD) at -20°C. Oxidation with CF3CO3H yielded pentathiane 3-oxide as the main product, whereas that of DMD gave 1- and 3-oxides. The structures of 1- and 3-oxides were finally determined by X-ray crystallographic analysis. DFT calculations of the NMR chemical shifts were performed on the chair and twist forms of the pentathiane and sixteen isomers of the monoxides with the GIAO method at the B3LYP/6-31G* level. The calculated chemical shifts were verified to be in practical agreement with the experimental data of the pentathiane and the isolated 1- and 3-oxides.

An S-oxide of 6-tert-butyl-6-phenylpentathiane. Structure in the crystalline state and in solution and thermal decomposition

Oxidation of 6-tert-butyl-6-phenylpentathiane with trifluoroperacetic acid gave the pentathiane 3-oxide mainly as the monooxide. The 3-oxide takes a twist conformation both in the crystalline state and in solution. Thermal decomposition of the 3-oxide in the presence of 2,3-dimethyl-1,3-butadiene yielded both S2O- and S2-transferred products.

A new simple synthesis of cis- and trans-3,5-di-tert-butyl-3,5-diaryl-1,2,4-trithiolanes from ketones and tetraphosphorus decasulfide

The reaction of pivalophenones with tetraphosphorus decasulfide afforded cis- and trans-3,5-di-tert-butyl-3,5-diaryl-1,2,4-trithiolanes, which equilibrated to give other isomers in refluxing toluene via thiopivalophenones and thiopivalophe-none S-sulfides.