31562-40-0

Usage

Synthesis Reference(s)

Tetrahedron Letters, 24, p. 3631, 1983 DOI: 10.1016/S0040-4039(00)88187-3

InChI:InChI=1/C8H18OS2/c1-7(2,3)10-11(9)8(4,5)6/h1-6H3

Upstream product

• 110-06-5 di-tert-butyl disulfide 
• 594-19-4 tert.-butyl lithium 
• 62383-66-8 tert-butylsulfenic tert-butylsulfinic dithioanhydride 
• 1608484-72-5 (R)-N-((S)-(2-(methoxymethoxy)phenyl)(phenyl)methyl)-2-methylpropane-2-sulfinamide 
• 116249-84-4 2-pyridyl tert-butyl sulfoxide 
• 75-66-1 2-methylpropan-2-thiol 
• 113548-13-3 N-(benzenesulfonyl)-3-phenyloxaziridine 
• 100-58-3 phenylmagnesium bromide 

Downstream Products

• 34637-31-5 2-Methyl-2-propyl-α-styrolthiolsulfinat 
• 4253-90-1 di-tert-butyl trisulfide 
• 5943-35-1 bis(2-methyl-2-propyl)tetrasulfide 
• 31562-41-1 di-tert-butyl thiosulfonate 
• 52754-01-5 2-methyl-2-propanesulfenic 2-methyl-2-propanesulfonic thioanhydride 
• 16537-17-0 3-chlorobenzoic acid tert-butyl ester 
• 112896-48-7 2-methyl-2-propyl 2-methyl-2-propanesulfinate 
• 887765-32-4 2-(tert-butylsulfinyl)-N,N-diisopropylbenzamide 
• 887765-41-5 2-(tert-butylsulfinyl)-N,N-diisopropyl-3-methoxybenzamide 
• 887765-40-4 2-(tert-butylsulfinyl)-N,N-diisopropyl-6-methoxybenzamide 
• 887765-42-6 2-(tert-butylsulfinyl)-N,N-diisopropyl-4-methoxybenzamide 
• 887765-43-7 2-(tert-butylsulfinyl)-N,N-diisopropyl-3,6-dimethoxybenzamide 
• 887765-44-8 2-(di-tert-butylphosphino)-6-(tert-butylsulfinyl)-N,N-diethylbenzamide 
• 887765-45-9 2-(tert-butylsulfinyl)-6-(dimethylamino)-N,N-diethylbenzamide 

Relevant academic research and scientific papers

Iodine mediated deprotection of N-tert-butanesulfinyl amines: A functional group compatible method

In the presence of iodine, a functional group compatible method for the deprotection of tert-butanesulfinyl and p-toluenesulfinyl units was developed. This journal is the Partner Organisations 2014.

The Chemistry of Alkylsulfenyl Alkylsulfinyl Thioanhydrides. The Mechanism of Decomposition

The decomposition mechanism of alkylsulfenyl alkylsulfinyl thioanhydrides has been investigated.Although the product mixture is complex in most cases, a detailed decomposition study as well as a careful analysis of the products allows for a proposal for a general mechanism which is interesting and not simple.We find, however, that the decomposition process is consistent with that of related systems.

Extremely Facile Ligand-Exchange and Disproportionation Reactions of Diaryl Sulfoxides, Selenoxides, and Triarylphosphine Oxides with Organolithium and Grignard Reagents

Diaryl sulfoxides undergo unusually rapid ligand-exchange reaction upon treatment with organolithium reagents at -95 deg C.Optically pure phenyl p-tolyl sulfoxide (4b) reacted with organolithium reagents at the range from -20 to -95 deg C to give facile ligand-exchange and disproportionation products, i.e., diphenyl sulfoxide (7), recovered 4b, and di-p-tolyl sulfoxide (8) in a statistical ratio of 1:2:1 in quantitative yields, and the recovered 4b was completely racemized.This facile ligand exchange was observed in the similar reactions using only diaryl selenoxides and triarylphosphine oxides.The reactions of 18O-labeled phenyl p-tolyl sulfoxide (4c) with organolithium reagents gave products in a statistical ration without 18O scrambling, indicating that only the C-S bond cleavage took place under low temperature.It is suggested that the ligand exchange reactions occur by the nucleophilic attack by organolithium reagent at the sulfinyl sulfur atom, giving ?-sulfurane as an intermediate that collapses rapidly.These results suggest that the treatment of arylic sulfoxides, selenoxides, and phosphine oxides with strong bases should be effected with caution.

Peroxidation of S-(2-Methyl-2-propyl) 2-Methyl-2-propanesulfinothioate

Oxidation of 1 equiv of S-(2-methyl-2-propyl) 2-methyl-2-propanesulfinothioate (1) with 2 equiv of m-chloroperoxybenzoic acid (MCPBA) gives S-(2-methyl-2-propyl) 2-methyl-2-propanesulfonothioate (4, 13percent), 2-methyl-2-propanesulfenic 2-methyl-2-propanesolfonic thioanhydride (5, 32percent), 2-methyl-2-propyl-3-chlorobenzoate (11, 4percent), 2-methyl-2-propyl 2-methyl-2-propanesulfinate (12, 22percent), and small amounts of bis(2-methyl-2-propyl) trisulfide (7) and bis(2-methyl-2-propyl) tetrasulfide (10).Possible mechanisms for product formation are discussed.

LIGAND EXCHANGE AND LIGAND COUPLING VIA THE ?-SULFURANE INTERMEDIATE IN THE REACTION OF ALKYL 2-PYRIDYL SULFOXIDE WITH GRIGNARD REAGENTS: CONVENIENT PREPARATION OF 2,2'-BIPYRIDINES

The reaction between methyl 2-pyridyl sulfoxide (1) with Grignard reagents afforded 2,2'-bipyridine (2) in moderate yield.The reaction is considered to involve initial ligand exchange to generate 2-pyridylmagnesium halide which in the subsequent step attacks the original sulfoxide to form the ?-sulfurane that undergoes ligand coupling to afford 2.The reaction of t-butyl-2-pyridyl sulfoxide (3) with C6H5MgBr, however, gave only 2-phenylpyridine (4).This may due to steric hindrance to the initial ligand exchange.Formation of 2 is a convenient process for preparation of 2,2'-bipyridines bearing various substituents.