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Preparation of N-(2-alkoxyvinyl)sulfonamides From N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

Preparation of N-(2-alkoxyvinyl)sulfonamides From N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

John M Bennett, Jonathan D Shapiro, Krystina N Choinski, Yingbin Mei, Sky M Aulita, Giovanny M Dominguez, Max M Majireck

J Vis Exp. 2018 Jan 3;(131):56848.

PMID: 29364238

Abstract:

Decomposition of N-tosyl-1,2,3-triazoles with rhodium(II) acetate dimer in the presence of alcohols forms synthetically versatile N-(2-alkoxyvinyl)sulfonamides, which react under a variety of conditions to afford useful N- and O-containing compounds. Acid-catalyzed addition of alcohols or thiols to N-(2-alkoxyvinyl)sulfonamide-containing phthalans provides access to ketals and thioketals, respectively. Selective reduction of the vinyl group in N-(2-alkoxyvinyl)sulfonamide-containing phthalans via hydrogenation yields the corresponding phthalan in good yield, whereas reduction with sodium bis(2-methoxyethoxy)aluminumhydride generates a ring-opened phenethylamine analogue. Because the N-(2-alkoxyvinyl)sulfonamide functional group is synthetically versatile, but often hydrolytically unstable, this protocol emphasizes key techniques in preparing, handling, and reacting these pivotal substrates in several useful transformations.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP15956282	Rhodium(II) acetate dimer		15956-28-2	Price

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