59121-52-7

Basic information

• Product Name: (1R)-(+)-thiocamphor S-oxyde
• CAS NO: 59121-52-7
• Molecular Weight: 184.302
• Mol File: 59121-52-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (1R)-(+)-thiocamphor S-oxyde(CAS DataBase Reference)
• NIST Chemistry Reference: (1R)-(+)-thiocamphor S-oxyde(59121-52-7)
• EPA Substance Registry System: (1R)-(+)-thiocamphor S-oxyde(59121-52-7)

Safety Data

• Hazardous Substances Data: 59121-52-7(Hazardous Substances Data)

Upstream product

• 52078-93-0 (1R)-(-)-thiocamphor 
• 53402-10-1 thiocamphor 
• 7519-74-6 (+/-)-thiocampher 

Downstream Products

• 464-49-3 (1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 
• 53402-10-1 thiocamphor 

Relevant articles and documents

Photochemical Oxidation of Thioketones by Singlet Molecular Oxygen Revisited: Insights into Photoproducts, Kinetics, and Reaction Mechanism

Photosensitized oxidation of trimethyl[2.2.1]bicycloheptane thioketones by 1O2 can yield more photoproducts than exclusively ketones and sulfines. Moreover, the ketone/sulfine ratio can be reversed when protic conditions and high thioketone concentrations are used, conversely to earlier results reporting ketones as the main photoproducts. A new mechanistic proposal for sulfine formation is suggested following intermolecular oxygen transfer from a peroxythiocarbonyl intermediate to a second thioketone molecule. Reaction quantum yields (10-5-10-2) depend on the reaction conditions and time. Sulfine production reaches a maximum at short irradiation times, whereas decomposition to the corresponding ketone is observed at long reaction times. When the thioketone substrate has a hydrogen atom at the α position a peroxyvinylsulfenic acid intermediate can be formed by proton transfer. Reaction of this intermediate with another thioketone molecule can yield more sulfine and its tautomeric vinylsulfenic acid, which dimerizes in situ to the thiosulfinate. The hydroperoxyl group of the peroxyvinylsulfenic acid can also rearrange to the α position, and by reaction with the starting thioketone, α-hydroxy thioketone and additional sulfine can be formed, while dehydration yields the α-oxo thioketone. In situ [2 + 2] and [4 + 2] self-cycloaddition of the α-oxo thioketone yields significant amounts of the corresponding adducts at prolonged irradiation times.

STERIC ASPECTS OF THE OXIDATION OF THIOKETONES BY SINGLET OXYGEN

Singlet oxygen oxidation of dialkyl thioketones yields the corresponding ketones and in some cases sulfoxides in varying amounts.Steric considerations on the reactive zwitterionic/diradical intermediates have been invoked to rationalise the product distribution.