137298-80-7Relevant 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
supporting information; 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
Copper-catalyzed addition of halide and sulfide groups to alkynes utilizing disulfides with tetrabutylammonium halides
Taniguchi, Nobukazu
, p. 849 - 852 (2008/12/22)
A copper-catalyzed addition of halide and sulfide groups to internal alkynes was carried out using disulfides with n-Bu4NX (X = Br, I or Cl) in air. The present reaction can selectively prepare the corresponding anti-configured haloalkenyl sulfide, and uses both sulfide groups of the disulfide reagent. Georg Thieme Verlag Stuttgart.
Stereo-recognizing transformation of (E)-alkenyl halides into sulfides catalyzed by nickel(0) triethyl phosphite complex
Yatsumonji, Yasutaka,Okada, Orie,Tsubouchi, Akira,Takeda, Takeshi
, p. 9981 - 9987 (2007/10/03)
(E)-Alkenyl halides were transformed into (E)-alkenyl sulfides by the nickel(0) triethyl phosphite complex-catalyzed reaction with thiols, whereas (Z)-alkenyl halides gave alkynes under the same reaction conditions. Aryl halides were also transformed into aryl sulfides using the same reagent system.
Free-Radical Reactions of Benzenethiol and Diphenyl Disulphide with Alkynes. Chemical Reactivity of Intermediate 2-(Phenylthio)vinyl Radicals
Benati, Luisa,Montevecchi, Pier Carlo,Spagnolo, Piero
, p. 2103 - 2109 (2007/10/02)
Reaction of benzenethiol at 100 deg C with neat alkyl- and dialkyl-acetylenes leads to virtually quantitative formation of isomeric mixtures of (E)- and (Z)-vinyl sulphide adducts in ratios which depend largely upon both the extent and the nature of alkyl substitution.Results are explained in terms of rapidly interconverting sp2-hybridized (E)- and (Z)-1-alkyl-2-(phenylthio)vinyl radical intermediates which can undergo hydrogen transfer from benzenethiol to an extent which is essentially dependent upon the steric hindrance of their cis-2-substituent.Consistent results are provided by related radical reactions of diphenyl disulphide with alkyl-substituted alkynes to afford varying amounts of 1,2-bis(phenylthio)ethylene adducts ascribable to SH2 reaction of the resulting 1-alkyl-2-(phenylthio)vinyl radicals with the disulphide present.Under analogous conditions benzenethiol and diphenyl disulphide react with phenylacetylenes to give vinyl sulphide or bissulphide adducts in a trans-stereoselective fashio.The findings are interpreted by suggesting, for the intermediate sp-hybridized 1-phenyl-2-(phenylthio)vinyl radicals, the occurrence of significant bonding interaction between the unpaired electron and the adjacent sulphur, which would essentially prevent attack of radical scavenger on the side cis to PhS.Evidence is also presented that 1-phenyl-2-(phenylthio)vinyl radicals can exhibit homolytic intramolecular cyclization reactions, leading to benzothiophene products to a comparatively much greater extent than the 1-alkyl-2-substituted analogues; however, 1-tert-butyl-2-(phenylthio)vinyl radical would represent a special case.
