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The reaction of N-phenylsulfonimidoyl chloride with trimethylsilylethene. A new route to 2-alkenylanilines

โœ Scribed by Michael Harmata; Mehmet Kahraman; Darin E. Jones; Neville Pavri; Susan E. Weatherwax

Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
684 KB
Volume
54
Category
Article
ISSN
0040-4020

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โœฆ Synopsis

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.

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The reaction of lithium trialkylalkynylb
The reaction of lithium trialkylalkynylborate with methanesulphinyl chloride. A novel route to internal acetylenes
โœ Mikio Naruse; Kiitiro Utimoto; Hitosi Nozaki ๐Ÿ“‚ Article ๐Ÿ“… 1973 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 215 KB

In continuation of the synthetic studies with trialkylalkynylborates,l this paper describes the reaction of these borates with methanesulphinyl chloride affording disubstituted acetylenes. To a stirred solution of phenylacetylene (0. 51 g, 5. 0 mmol) in THF (5 ml) at 0' maintained