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Sulfanyl radical addition to alkynyl azides: an insight into vinyl radical cyclization onto the azido function

✍ Scribed by Pier Carlo Montevecchi; Maria Luisa Navacchia; Piero Spagnolo

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
230 KB
Volume
38
Category
Article
ISSN
0040-4039

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✦ Synopsis

5-Exo-Cyclization of 2-sulfanylvinyl radicals 16 and 21 is a fast process which prevents intramolecular addition to the sulfanyl aromatic ring and hydrogen abstraction. In contrast, the 2sulfanylvinyl radicals 3 and 9 are reluctant to add to their aliphatic azido subslituent either in a ~-(endo) ~ in a rc-(exo) mode. These radicals exclusively undergo cyclization onto the adjacent aromatic ring and H-transfer from the thiol present.

πŸ“œ SIMILAR VOLUMES

A Study of Vinyl Radical Cyclization ont
A Study of Vinyl Radical Cyclization onto the Azido Group by Addition of Sulfanyl, Stannyl, and Silyl Radicals to Alkynyl Azidesβ˜†
✍ Pier Carlo Montevecchi; Maria Luisa Navacchia; Piero Spagnolo πŸ“‚ Article πŸ“… 1998 πŸ› John Wiley and Sons 🌐 English βš– 621 KB

Thermal radical reactions of azidoalkynes 2, 8, 14, and 21ac with thiols 1a-c afford 2-sulfanylvinyl radicals by selective addition of sulfanyl radicals to the triple bond. 1-Phenylvinyl radicals 23 and 30a, as well as vinyl radical 30b, undergo fast 5-cyclization onto the aromatic azide function to