54784-92-8Relevant academic research and scientific papers
A new method for the activation of ethyl benzenesulfenate in electrophilic addition reactions
Zyk,Gavrilova, A. Yu.,Mukhina,Bondarenko,Zefirov
experimental part, p. 2572 - 2578 (2010/05/02)
Reactions of unsaturated compounds with the PhSOEt-SOHal2 and PhSOEt-Me3SiHal systems (Hal = Cl or Br) were proposed as a new route to haloalkyl phenyl sulfides. With acyclic and mono- and bicyclic alkenes and dienes as examples, the
A convenient method for bromosulfenylation: Reactions of sulfenamides with olefins in the presence of POBr3
Zyk, Nikolai V.,Beloglazkina, Elena K.,Gazzaeva, Rimma,Tyurin, Vladimir S.,Titanyuk, Igor D.
, p. 33 - 45 (2007/10/03)
A general method for the one-pot transformation of alkenes into abromoalkyl-arylsulfides has been proposed based on the sulfenylation reaction by means of sulfenamides in the presence of phosphorus oxibromide. The plausible reaction mechanism and the results of reactions with a number of model alkenes such as cyclohexene, 1-heptene, norbornene and other from the bicyclo[2.2.1]heptane series are discussed.
Synthetic utility of 4'-nitrobenzenesulfenanilide in the functionalization of carbon-carbon double and triple bonds: Its use in the bromosulfenylation of alkenes and alkynes
Benati,Montevecchi,Spagnolo
, p. 5365 - 5376 (2007/10/02)
The reaction of 4'-nitrobenzenesulfenanilide (NBSA) with hydrobromic acid, suitably carried out at room temperature in the presence of cyclohexene, trans-hex-3-ene, hex-1-ene and 3,3-dimethylbut-1-ene, results in quantitative isolation of corresponding 2-bromoalkyl phenyl sulfides which occur with trans-stereospecificity and anti-Markovnikov regiospecificity through electrophilic addition of initially-formed benzenesulfenyl bromide to the alkene double bond. Similar reaction in the presence of mono- and di- substituted alkyl- and phenyl-acetylenes generally affords (E)-2-bromovinyl phenyl sulfides in good yields, which become lower with decreasing nucleophilic power of the alkyne employed. However, in the presence of parent acetylene, no virtual formation of the corresponding sulfide adduct occurs, but almost exclusive formation of diphenyl disulfide essentially ascribable to preferred decomposition of the highly unstable benzenesulfenyl bromide intermediate. The present additions of benzenesulfenyl bromide to alkenes and alkynes are believed to involve the initial intermediacy of thiiranium- and thiirenium-like ions, respectively, by analogy with related Ad(E) reactions of sulfenyl chlorides.
ELECTROPHILIC SULFAMATOSULFENYLATION OF OLEFINS
Zefirov, N.S.,Zyk, N.V.,Kutateladze, A.G.,Lapin, Yu.A.
, p. 351 - 360 (2007/10/02)
The reaction of N,N-dialkylarenesufenamides with sulfur trioxides gave arenesulfenyl sulfamates, which have clearly defined electrophilic characteristics.These reagents are capable of adding at the C=C bond of olefins with the formation of the sulfamates of arylthio-substituted alcohols.The reaction with cyclohexene is stereospecific and leads to the trans-1,2-adducts, while the reaction with norbornene and norbornadiene is accompanied by rearrangement of the carbon framework.For the case of the cyclohexane derivatives it was shown that the vicinal arylthiosulfamates are highly sensitive to nucleophilic reagents.
