128787-41-7Relevant articles and documents
Synthesis of 2-fluoro-3-phenylthio-1,3-butadiene and 2-trifluoromethyl-3- phenylthio1,3-butadiene and their reactivities toward various dienophiles
Paul, Kamaldeep,Hwang, Ji Hye,Choi, Ji Hoon,Jeong, In Howa
supporting information; experimental part, p. 4728 - 4731 (2009/12/07)
A general approach for the synthesis of novel 2-fluoro-3-phenylthio-1,3- butadiene (8) and 2-trlfluoromethyl-3-phenylthlo-1,3-butadiene (9) from monobromoalkene and dibromoalkenes has been developed. Subsequent Dlels-Alder reactions of these dienes with s
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.