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A Study of Vinyl Radical Cyclization onto the Azido Group by Addition of Sulfanyl, Stannyl, and Silyl Radicals to Alkynyl Azides☆

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

Publisher: John Wiley and Sons
Year: 1998
Tongue: English
Weight: 621 KB
Volume: 1998
Category: Article
ISSN: 1434-193X
DOI: 10.1002/(sici)1099-0690(199806)1998:6<1219::aid-ejoc1219>3.0.co;2-v

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✦ Synopsis

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 give cyclized indoles. In contrast, both 1-phenyl (15, 17) and 1-alkyl (3a,b, 9) vinyl radicals fail to add to their aliphatic azido substituents and exclusively undergo cyclization onto the aromatic sulfanyl ring and H transfer from the thiol precursor.

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