91525-58-5Relevant academic research and scientific papers
Indium(III) chloride-catalyzed thiolysis of meso-aziridines
Peruncheralathan, Saravanan,Henze, Michael,Schneider, Christoph
, p. 6743 - 6746 (2007)
Indium(III) chloride efficiently catalyzed the thiol addition to meso-aziridines at very low substrate-catalyst ratios giving rise to 1,2-amino sulfides in excellent yields and complete diastereocontrol.
A highly efficient and general method for the ring-opening of aziridines with various nucleophiles in DMSO
Wu, Jie,Sun, Xiaoyu,Sun, Wei
, p. 4231 - 4235 (2008/09/18)
Ring-opening of aziridines with various nucleophiles (such as amines, thiols, and silylated nucleophiles) in DMSO under mild conditions without any catalyst afforded the corresponding products in good to excellent yields. The Royal Society of Chemistry 20
Boron Trifluoride-Promoted Reaction of Benzenesulphenanilides with Alkenes in Acetonitrile and Benzonitrile: Amidino- and Amido-sulphenylation of Alkenes
Benati, Luisa,Montevecchi, P. Carlo,Spagnolo, Piero
, p. 2815 - 2818 (2007/10/02)
Benzenesulphenanilides (1) react at room temperature with alkenes in acetonitrile or benzonitrile in the presence of boron trifluoride-diethyl ether to give amidino sulphides (5; R=Me, Ph) in fair to good yields together with varying amounts of amido sulphides (7; R=Me, Ph) and arylamino sulphides (4), whereas at 100 deg C and in the presence of water 4'-nitrobenzenesulphenanilide affords amido sulphides (7; R=Me, Ph) as the main products.With cyclohexene a high selectivity for trans-addition is observed.With terminal alkenes the terminal sulphides are produced with high regioselectivity.The findings are consistent with a mechanism involving intermediacy of episulphonium ions (3) which result from alkene attack at the sulphur atom of an anilide-BF3 complex.
BORON TRIFLUORIDE PROMOTED REACTION OF BENZENESULPHENANILIDES WITH ALKENES
Benati, Luisa,Montevecchi, P. Carlo,Spagnolo, Piero
, p. 1145 - 1156 (2007/10/02)
The boron trifluoride-promoted reaction of a series of 3'- and 4'-substituted benzenesulphenanilides (1) with various alkenes has been investigated as a potential synthetic route to arylaminosulphides.The benzenesulphenanilides (1) investigated generally afford arylaminosulphenylation adducts in fair to good yields except for the methoxy-substituted anilides (1e and f), which largely lead to decomposition products under comparable conditions.In all cases examined, the addition proceeds with trans-stereospecificity and, with terminal alkenes, leads regioselectively to the exclusive (or predominant) formation of the terminal sulphides.The findings are interpreted by assuming that boron trifluoride transforms the sluggish benzenesulphenanilides (1) into reactive electrophilic species, which can undergo nucleophilic attack at sulphur by an alkene, presumably affording episulphonium-borate ion-pair intermediates, in competition with attack by another sulphenanilide unit.
BORON TRIFLUORIDE PROMOTED REACTION OF BEZENESULPHENANILIDES WITH ALKENES-ARYLAMINOSULPHENYLATION OF ALKENES.
Benati, L.,Montevecchi, P.C.,Spagnolo, P
, p. 2039 - 2042 (2007/10/02)
The addition of benzenesulphenanilides to alkenes in the presence of boron trifluoride provides a practicable synthetic procedure for the arylaminosulphenylation of alkenes.
