The reaction of N-phenylsulfonimidoyl chloride with trimethylsilylethene. A new route to 2-alkenylanilines
N-Phenylsulfonimidoyl chloride reacts with trimethylsilylethene in the presence of aluminum chloride to give two product benzothiazines, one of which has been desilylated. The silylated benzothiazine can be deprotonated and alkylated, sometimes with very high diastereocontrol. Upon treatment with fluoride, these silylated benzothiazines undergo desilylation with concomitant cleavage of the carbon-sulfur bond to give 2- alkenylsulfinanilides which can be hydrolyzed to the corresponding anilines.
Harmata, Michael,Kahraman, Mehmet,Jones, Darin E.,Pavri, Neville,Weatherwax, Susan E.
p. 9995 - 10006
(2007/10/03)
Preparation of amines from olefins using certain transition metal catalysts
Aliphatic and aromatic amines are produced by reacting an olefin with either ammonia or a primary or secondary amine in the presence of a catalytic amount of ruthenium or iron compound catalyst. The reaction is carried out in the liquid phase using an inert liquid, a product amine, or one of the reactants as a solvent. The temperatures used are 100° to 250° C. and the pressures are at least autogenous and up to 12,000 psig.
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(2008/06/13)
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