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Selective monosulfonylation of internal 1,2-diols catalyzed by di-n-butyltin oxide

โœ Scribed by Michael J Martinelli; Rajappa Vaidyanathan *; Vien Van Khau

Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
115 KB
Volume
41
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

The reaction of internal 1,2-diols with catalytic n-Bu 2 SnO, p-TsCl (1.05 equiv.) and Et 3 N (1.1 equiv.) led to selective monotosylation. In the case of cyclic substrates, the cis-1,2-diol moiety appeared best suited for optimal results, supporting the intermediacy of a five-membered chelate.

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Selective sulfonylation of 1,2-diols and
Selective sulfonylation of 1,2-diols and derivatives catalyzed by a recoverable fluorous tin oxide
โœ Brian Bucher; Dennis P Curran ๐Ÿ“‚ Article ๐Ÿ“… 2000 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 72 KB

Fluorous tin oxide (C 6 F 13 CH 2 CH 2 ) 2 SnO is readily synthesized, exhibits spectra that are generally similar to dibutyltin oxide and appears to exist as an oligomer or polymer. The fluorous tin oxide can be used catalytically to effect the selective monotosylation of 1,2-diols with TsCl/Et 3 N