163840-05-9Relevant academic research and scientific papers
Reaction of 4′-nitrobenzenesulfenanilide (NBSA) with Lewis acids. A study of its application in sulfenocyclization of alkenes and alkynes
Benati, Luisa,Capella, Laura,Montevecchi, Pier Carlo,Spagnolo, Piero
, p. 12395 - 12406 (2007/10/02)
Phenylsulfenocyclization of a number of alkenes and alkynes possessing internal hydroxyl, carboxyl or vinyl functionality has been investigated with NBSA. Thioetherification of 4-penten-1-ol 4 as well as thiolactonization of 4-penten-1-oic acid 7 and, to a modest extent, 4-pentyn-1-oic acid 8 can be successfully achieved with NBSA in the presence of boron trifluoride. On the other hand, under analogous conditions 3-buten-1-ol 3 and 3-buten-1-oic acid 6 fail to undergo thiocyclization and give instead oxa- and/or aza-sulfenylation 1,2-adducts. Similar failure is observed with 4-pentyn-1-ol 5, in which case diphenyl disulfide and 4-nitroaniline are the exclusive products. Hexa-1,5-diene 9, to some extent, affords a cyclized arylaminosulfide, i.e. 23, ascribable to formal loss of a methylene unit from the initial (phenylthiomethyl)- cyclopentyl cation 24. The reaction products are discussed in terms of intermediate thiiranium and thiirenium ions whose decomposition mode is strictly dependent upon their structural features. Novel evidence is also presented that aluminium chloride and bromide can promote reaction of NBSA with alkenes and alkynes to afford chloro- and bromo-sulfenylation adducts in varying yields.
Elimination and Addition Reactions. Part 37. A Comparative Study of Electronic, Steric , and Solvent Effects upon Reactivity in Additions of Benzenesulphenyl Chloride to Alkenes
Jones, G. Alun,Stirling, Charles J. M.,Bromby, Norman G.
, p. 385 - 394 (2007/10/02)
Rates of additions of benzenesulphenyl chloride to 35 alkenes in several solvents have been measured, and the products of the reactions have in most cases been identified.Results for arylalkenes broadly confirm previous work, but the responses to solvent change are not uniform throughout.The reactivity of bridged cycloalkanes is substantially greater than that of cycloalkenes, but that of cyclo-pentadiene dimer is anomalously small.For allylic substrates, the correlation of electron density at the double bond with reactivity is shown by a rectilinear relationship between log k and ?I.Allyl iodide and allyl alcohol are anomalously more reactive than this correlation would predict; this is accounted for by solvation and by internal solvation effects respectively.
O-SILYLATED ENOLATES IN ORGANIC SYNTHESIS: SULPHUR-MEDIATED ALKYLATION OF ESTERS WITH ALKENES.
Patel, Shailesh K.,Paterson, Ian
, p. 1315 - 1318 (2007/10/02)
O-Silylated ester enolates can be alkylated, under ZnBr2-catalysis, by the PhSCl-adducts of mono- and di-substituted alkenes to give γ-phenylthioesters, from which sulphur can be removed both reductively and oxidatively.This alkene carbosulphenylation rea
