128787-43-9Relevant academic research and scientific papers
Generation and reactions of thiirenium ions by the Cation Pool method
Shimizu, Akihiro,Horiuchi, Shun,Hayashi, Ryutaro,Matsumoto, Kouichi,Miyamoto, Yu,Morisawa, Yusuke,Wakabayashi, Tomonari,Yoshida, Jun-Ichi
, p. 97 - 113 (2018/02/07)
Thiirenium ions generated and accumulated by low-temperature electrochemical oxidation of disulfides in the presence of alkynes were successfully observed by low-temperature NMR, Raman, and mass spectroscopies and were found to be stable at temperatures below -40 °C. The thiirenium ions showed ambident reactivity toward subsequently added nucleophiles to give either disubstituted alkenes or alkynes depending on the nature of the nucleophiles.
Phenylthio (and phenylseleno)fluorination of alkenes and alkynes using N-phenylthio (and phenylseleno)phthalimide combined with pyridine*9HF or Et3N*3HF complexes
Saluzzo, Christine,Spina, Anna-Maria La,Picq, Dominique,Alvernhe, Gerard,Anker, Daniel,et al.
, p. 831 - 843 (2007/10/02)
N-Phenylthiophthalimide and N-phenylselenophthalimide combined with pyridine*9HF or Et3N*3HF complexes allow the formal addition of elements of PHSF or PhSeF across the carbon-carbon double or triple bond by a one-pot reaction.Pyridine*9HF, a strongly aci
Boron Trifluoride-promoted Reaction of 4'-Nitrobenzenesulphenanilide with Alkynes. Formal Addition of Benzenesulphenyl Fluoride to Carbon-Carbon Triple Bonds
Benati, Luisa,Montevecchi, P. Carlo,Spagnolo, Piero
, p. 1690 - 1695 (2007/10/02)
The BF3-promoted reaction of 4'-nitrobenzenesulphenanilide with simple alkyl- and aryl-alkynes at 80 deg C in the presence of tetrabutylammonium tetrafluoroborate provides a one-pot synthetic route to β-fluorovinyl sulphides via a formal regioselective and trans-stereospecific addition of benzenesulphenyl fluoride towards carbon-carbon triple bonds.
ELECTROPHILIC ADDITION OF 4'-NITROBENZENESULPHENANILIDE TO ALKYNES, EFFECTS OF ARYL AND ALKYL SUBSTITUENTS AT RING CARBONS OF INTERMEDIATE THIIRENIUM IONS
Benati, Luisa,Montevecchi, Pier Carlo,Spagnolo, Piero
, p. 609 - 616 (2007/10/02)
The BF3-promoted addition of 4'-nitrobenzenesulphenanilide, NBSA, to a number of aryl- and alkyl-acetylenes has been investigated in dichloromethane, p-xylene and/or benzene.Diphenylacetylene, 1a, 1-phenylbutyne, 1b, and 1-phenylpropyne, 1c, generally lead to 1,2-bis(phenylthio)alkenes 4a-c, and N-(4-nitrophenyl)-S-phenyl-S-(2-phenylthiovinyl)sulphimides, 6a-c, in fair to good yields with trans stereospecificity.Phenylacetylene, 1d, similarly gives the corresponding bis(phenylthio)adduct 4d and sulphimide 6d in dichloromethane, but in the aromatic solvents these products are essentially suppressed in favour of 1-aryl-1-phenyl-2-(phenylthio)ethylenes 7d.On the other hand, alkyl- and, particularly, dialkyl-substituted acetylenes preferentially afford β-fluorovinyl sulphides, 5, with trans stereospecifity.These findings are interpreted in terms of a different reactivity towards nucleophilic attack of the intermediate aryl- and alkyl-trihirenium ions which would result from electrophilic sulphenylation of the corresponding alkynes.Steric effects of the substituents are believed to play a major role in determining the different reactivity observed.
