16797-76-5

Basic information

• Product Name: 1-Butene-1-thione, 2-(1,1-dimethylethyl)-3,3-dimethyl-, S-oxide
• Synonyms: 2-tert-butyl-3,3-dimethyl-1-sulfinyl-1-butene
• CAS NO: 16797-76-5
• Molecular Formula: C₁₀H₁₈OS
• Molecular Weight: 186.31432
• Mol File: 16797-76-5.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-Butene-1-thione, 2-(1,1-dimethylethyl)-3,3-dimethyl-, S-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Butene-1-thione, 2-(1,1-dimethylethyl)-3,3-dimethyl-, S-oxide(16797-76-5)
• EPA Substance Registry System: 1-Butene-1-thione, 2-(1,1-dimethylethyl)-3,3-dimethyl-, S-oxide(16797-76-5)

Safety Data

• Hazardous Substances Data: 16797-76-5(Hazardous Substances Data)

Upstream product

• 19824-34-1 di-tert-butylketene 
• 29571-65-1 2-tert-butyl-3,3-dimethyl-butyryl chloride 
• 54396-68-8 3-diazo-2,2,4,4-tetramethylpentane 
• 756860-83-0 3,3-di-tert-butylthiirane-2-thione S-oxide 
• 16797-75-4 di-tert-butylthioketene 
• 67-56-1 methanol 

Downstream Products

• 66124-44-5 (2-tert-Butyl-3,3-dimethyl-but-1-ene-1-sulfinyl)-benzene 
• 66124-47-8 2-Benzenesulfinyl-3-tert-butyl-4,4-dimethyl-pent-2-enoic acid phenylamide 

Relevant articles and documents

REACTIONS OF THIOKETEN S-OXIDES WITH DIAZO COMPOUNDS A NOVEL SYNTHESIS OF HETEROCYCLIC SULFINES

Thioketen S-oxides 1 react with 2-diazopropane (2a) to give 1-pyrazoline-4-thione S-oxides 3.Addition of diazomethane to 1 yields a stable 1:1-adduct only from the S-oxide 1c.The constitution of both types of cycloadducts (3, 11) was proven by X-ray diffraction.Irradiation of 3 leads to loss of nitrogen to afford the alkylidene thiirane S-oxides 12.

Synthesis and reaction of α-dithiolactone

Treatment of di-tert-butylthioketene S-oxide (5a) with Lawesson reagent at room temperature resulted in the formation of 3,3-di-fert-butylthiirane-2-thione (4a) in high yield. The oxidation of 4 a with mCPBA (mCPBA = m-chloroperbenzioc acid) gave 3,3-di-ferf-butylthiirane-2-thione S-oxide (6) almost quantitatively. The reactions of 4 a with dimethyl acetyle nedicarboxylate (DMAD) and benzyne afforded dimethyl 2-(2,2,4,4-tetramethylpentan-3-ylidene)-1, 3-dithiole-4,5-dicarboxylate (13) and 2-(2,2,4,4-tetramethylpentan-3-ylidene) benzo[d] [1,3]-dithiole (15), respectively, in high yields, suggesting that 4 a is an excellent 1,3-dipole. The reaction of 4 a with ethylenebis(triphenylphosphine)platinum (16) gave dithiolato-platinum complex (22) in high yield. The structure of 22 was determined by X-ray crystallographic analysis.

Oxidation of Thioketens by Singlet Oxygen and Ozone

Di-t-butylthioketen (1) readily reacts with singlet oxygen to yield unexpected products (based on the behaviour of other heterocumulenes) and reacts with ozone to give, quantitatively, the corresponding sulphoxide (2).