45734-11-0

Upstream product

• 62891-12-7 1,3,2-dioxaphosphorinane, 5,5-dimethyl-2-(1-methylethoxy)-, 2-sulfide 
• 100-66-3 methoxybenzene 

Downstream Products

• 87763-36-8 N,N'-dibenzyl-N-(5,5-dimethyl-2-oxo-1,3,2-dioxaphosphorinanyl)-thiourea 
• 15762-04-6 5,5-dimethyl-2-oxo-1,3,2-dioxaphosphorinan-2-yl 5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl-oxide 
• 1212-29-9 1,3-dicyclohexylthiourea 
• 87763-32-4 N,N'-dicyclohexyl-N-(5,5-dimethyl-2-oxo-1,3,2-dioxaphosphorinanyl)-thiourea 

Relevant academic research and scientific papers

Thiono-Thiolo Rearrangement and Solvolysis of the Secondary Alkyl Phosphorothionates. 3

The protic acid catalyzed thiono-thiolo (O->S) migration of secondary alkyl groups in trialkyl phosphorothionates 1 occurs in a complex fashion.Analysis of product distribution, stereochemistry, and deuterium incorporation experiments supports an ion-pair-type intermediate, 7, as being responsible for the entire process.Nucleophilic attack by 1 on 7 initiates the chain reaction leading to 2.In trifluoroacetic acid medium inversion of configuration (96percent) at the carbon atom of the migration sec-butyl group was observed.A high concentration of 1 promotes this mode of rearrangement.However, the overall stereospecificity of sec-butyl migration is much lower due to an elimination process leading to the dialkyl hydrogen phosphorothioate 3 and an intermediate olefin which after protonation in acidic medium returns to the ion pair 7.The latter process is responsible for the nonstereospecific formation of part of the rearrangement product 2 and contributes to the lower stereospecificity of the trifluoroacetolysis process.The role of reaction-medium acidity is discussed.