152959-18-7Relevant academic research and scientific papers
Copper-catalyzed synthesis of β-haloalkenyl chalcogenides by addition of dichalcogenides to internal alkynes and its application to synthesis of (Z)-tamoxifen
Taniguchi, Nobukazu
experimental part, p. 2782 - 2790 (2009/08/15)
A copper-catalyzed synthesis of β-haloalkenyl sulfides or selenides was carried out by addition of dichalcogenides and tetrabutylammonium halides to internal alkynes. The present reaction anti- and regio-selectively afforded the corresponding alkenyl chal
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.
