50404-35-8

Basic information

• Product Name: Bicyclo[2.2.1]heptane-2-thione, 1,7,7-trimethyl-, S-oxide
• CAS NO: 50404-35-8
• Molecular Formula: C10H16OS
• Molecular Weight: 184.302
• Mol File: 50404-35-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Bicyclo[2.2.1]heptane-2-thione, 1,7,7-trimethyl-, S-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: Bicyclo[2.2.1]heptane-2-thione, 1,7,7-trimethyl-, S-oxide(50404-35-8)
• EPA Substance Registry System: Bicyclo[2.2.1]heptane-2-thione, 1,7,7-trimethyl-, S-oxide(50404-35-8)

Safety Data

• Hazardous Substances Data: 50404-35-8(Hazardous Substances Data)

Upstream product

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

Downstream Products

• 59056-01-8 1,7,7-Trimethyl-2-phenylmethanesulfinyl-bicyclo[2.2.1]hept-2-ene 
• 59056-13-2 1-(4-Bromo-phenyl)-2-(1,7,7-trimethyl-bicyclo[2.2.1]hept-2-ene-2-sulfonyl)-ethanone 
• 59056-08-5 1,7,7-Trimethyl-2-phenylmethanesulfonyl-bicyclo[2.2.1]hept-2-ene 
• 59056-06-3 1-(4-Bromo-phenyl)-2-(1,7,7-trimethyl-bicyclo[2.2.1]hept-2-ene-2-sulfinyl)-ethanone 

Relevant articles and documents

Reaction of Thioketones with Carbonyl Oxides and 3,3-Dimethyl-1,2-dioxirane. Cycloaddition vs. Oxygen Atom Transfer

The ozonolysis of vinyl ethers 1a, b in the presence of adamantane-2-thione 4a and bicyclononan-9-thione 4b gave in each case the corresponding thioozonides 5a-c in moderate yields, whilst ozonolysis of a mixture of vinyl ethers 1a-d and thiobenzophenone derivatives 4f-h gave the corresponding thione S-oxides 8f-h in isolated yields of 10-40percent, together with the benzophenones 7f-h. 3,3-Dimethyl-1,2-dioxirane, generated in situ from the reaction of acetone and 'oxone' (2KHSO5-KHSO4-K2SO4), transferred an oxygen atom to compounds 4a, f, g, i providing the thione S-oxides 8a, f, g, i in 29-97 percent yield.

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.