82993-63-3Relevant articles and documents
Acetamidinosulphenylation of Alkynes via Electrophilic Addition of 4'-Substituted Benzenesulphenanilides in Acetonitrile
Benati, Luisa,Montevecchi, P. Carlo,Spagnolo, Piero
, p. 1105 - 1111 (2007/10/02)
A number of 4'-substituted benzenesulphenanilides and N-methyl-4'-nitrobenzenesulphenanilide are shown to add to simple alkynes in acetonitrile in the presence of boron trifluoride-diethyl ether to give acetamidinovinyl sulphides in varying yields.Addition is largely favoured by dialkyl substitution on the alkyne and by electron-attracting anilide substituents.Moreover, the azasulphenylation adducts are produced with trans stereospecificity and high regioselectivity (Markovnikov orientation).A likely mechanism involves nucleophilic displacement by the alkyne at the activated sulphur of the anilide complexed with boron trifluoride leading to the initial formation of a thiirenium ion intermediate.Subsequent back-side attack of acetonitrile on the thiirenium ion gives a nitrilium ion which is ultimately trapped by the liberated arylamine.
Benzenesulphenanilidyl Radicals. Part 3. Reactions of 4'-Substituted Benzenesulphenanilides with t-Butoxyl Radicals
Benati, Luisa,Montevecchi, P. Carlo,Spagnolo, Piero
, p. 1577 - 1582 (2007/10/02)
Decomposition products of the 4'-substituted benzenesulphenanilidyl radicals (2a, b, d, and e), generated from the corresponding benzenesulphenanilides (1) with t-butoxyl radicals, have been investigated in benzene, acetonitrile, and acetone.Results indicate that the decomposition modes exhibited by these radicals are not essentially influenced by variation of the solvent polarity; comparison of the findings with present and previous results from oxidation of (1) with lead dioxide show that the chemical reactivity trend displaced by the thioaminyls (2) can be greatlyinfluenced both by the reaction medium and the 4'-substituent.Evidence is presented that the benzenesulphenanilides (1b) and (1e) react in acetone in the presence of di-t-butyl hyponitrite to give products ascribable to homolytic substitution at the sulphenanilide sulphur by acetonyl radicals.
The Conjugated N,N'-(Polyenediylidene)bis-sulphenamide Chromophore. Part I. N,N'-Bisarylthio-quinone Diimines
Shand, Charles A.,Thomson, Ronald H.,Greenhalgh, Colin W.
, p. 1601 - 1617 (2007/10/02)
N,N'-Bisarylthio-quinone diimines have been prepared from p-phenylenediamines and arenesulphenyl chlorieds, and from N,N'-dichloroquinone diimines and thiols.They are intensely coloured (the N,N'-dialkyl derivatives also) and exhibit Z/E isomerism in solu
