54440-00-5

Basic information

• Product Name: Methanethione, (2,2,6,6-tetramethylcyclohexylidene)-
• Synonyms: Methanethione,(2,2,6,6-tetramethylcyclohexylidene);1,1,3,3-tetramethyl-2-(thiocarbonyl)cyclohexane;2,2,6,6-tetramethylcyclohexylidenemethanethione;1,1,3,3-tetramethyl-2-thiocarbonylcyclohexan
• CAS NO: 54440-00-5
• Molecular Formula: C11H18S
• Molecular Weight: 182.33
• Mol File: 54440-00-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Methanethione, (2,2,6,6-tetramethylcyclohexylidene)-(CAS DataBase Reference)
• NIST Chemistry Reference: Methanethione, (2,2,6,6-tetramethylcyclohexylidene)-(54440-00-5)
• EPA Substance Registry System: Methanethione, (2,2,6,6-tetramethylcyclohexylidene)-(54440-00-5)

Safety Data

• Hazardous Substances Data: 54440-00-5(Hazardous Substances Data)

Upstream product

• 67-66-3 chloroform 
• 63702-84-1 2,2,6,6-tetramethylcyclohexanethione 
• 1195-93-3 2,2,6,6-tetramethylcyclohexanone 
• 83357-68-0 2,2,6,6-Tetramethyl-cyclohexanmethanol 
• 13377-52-1 2.2.6.6-Tetramethyl-cyclohexan-carbonsaeure-⁽¹⁾ 
• 29779-78-0 1,1,3,3-Tetramethyl-2-methylencyclohexan 
• 29779-72-4 1,2,2,6,6-Pentamethyl-1-cyclohexanol 
• 54439-96-2 2,2,6,6-Tetramethylcyclohexancarbonylchlorid 
• 63702-87-4 (2,2,6,6-tetramethylcyclohexylidene)methanethione S-oxide 

Downstream Products

• 98687-84-4 2-Methoxy-4,4,8,8-tetramethyl-1-thia-spiro[2.5]octane 
• 98687-87-7 2,2,6,6-Tetramethyl-cyclohexanecarbothioic acid O-methyl ester 
• 98687-83-3 1,2-Bis-(2,2,6,6-tetramethyl-cyclohexyl)-ethane-1,2-dione 
• 98687-85-5 2-Ethoxy-4,4,8,8-tetramethyl-1-thia-spiro[2.5]octane 
• 98687-88-8 2,2,6,6-Tetramethyl-cyclohexanecarbothioic acid O-ethyl ester 
• 84662-15-7 2,2-Dimethyl-5-(2,2,6,6-tetramethylcyclohexyliden)-Δ³-1,3,4-thiadiazolin 
• 103-19-5 di(p-tolyl) disulfide 
• 112222-20-5 (4-Methylphenyl)-(2,2,6,6-tetramethylcyclohexancarbonyl)-disulfid 
• 112222-18-1 2,2,6,6-Tetramethyl-N-tosylcyclohexancarboxamid 
• 112221-20-2 5,5,9,9-Tetramethyl-3-thioxo-2-tosyl-2-azaspiro<3.5>nonan-1-on 
• 112222-19-2 5-(2,2,6,6-Tetramethylcyclohexyl)-N-tosyl-3H-1,2,4-dithiazol-3-imin 
• 107825-70-7 [2-Methylsulfanyl-1-phenyl-2-(2,2,6,6-tetramethyl-cyclohexylidene)-ethyl]-[1-phenyl-meth-(E)-ylidene]-amine 
• 1195-93-3 2,2,6,6-tetramethylcyclohexanone 
• 88131-22-0 methyl 3,3,7,7-tetramethyl-2-oxocycloheptanesulfinate 

Relevant articles and documents

Reactions of thioketones with dichlorocarbene

The reactions of sterically crowded cycloalkanethiones of type 2 with CHCl3/NaOH under phase-transfer catalysis (PTC) with benzyl(triethyl)ammonium chloride (TEBA) as catalyst afforded the corresponding 'gem.-dichlorothiiranes' of type 3 in good yields (cf. Scheme 2 and Table). The desulfurization, which, in some cases, occurred spontaneously, led to (dichloromethylidene)cycloalkanes of type 4. Similar results were obtained using Seyferth's reagent in boiling benzene. In the case of 2,2,6,6-tetramethylcyclohexanethione, reaction under PTC conditions after 3 h yielded only the corresponding dichloromethylidene derivative; on the other hand, workup after 1 h gave (2,2,6,6- tetramethylcyclohexylidene)methanethione (thioketene 9; Scheme 5).

Gas-phase Thermolysis of a Thioketen-S-Oxide

The unimolecular gas-phase thermolytic decomposition of 1,1,3,3-tetramethyl-2-thiocarbonylcyclohexane S-oxide (3) has been studied as a function of temperature by a flash vacuum thermolysis (f.v.t.) technique.The products detected are the carbenes (4) and (5), the ketone (6), the keten (7), the thioketone (8), and the thioketen (9).The product ratio is highly dependent on the thermolysis temperature.The thermolysis of (3) is mechanistically rationalized by assuming the existence of only two concurrent primary processes, which are (a) extrusion of atomic oxygen, leading to the thioketen (9), and (b) electrocyclic ring closure into the corresponding three-membered oxathiiran (10).The latter is dominant at lower temperatures, whereas higher thermolysis temperatures favour atomic oxygen extrusion.At further elevated temperatures additional concurrent primary reactions, i.e. extrusions of SO and CSO leading to the carbenes (5) and (4), respectively, are observed.Owing to an apparently very short half-life of the oxathiiran (10), only the decomposition products of the three-membered ring compound have been detected.These are the thioketone (8), formed by rearrangement of (10) into the α-thiololactone (11) followed by loss of CO, minor amounts of the ketone (6), formed analogously, and the keten (7), as a result of simple sulphur extrusion.