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Five vs six membered ring formation in the vinyl radical cyclization

✍ Scribed by Gilbert Stork; Robert Mook Jr.

Publisher: Elsevier Science
Year: 1986
Tongue: French
Weight: 153 KB
Volume: 27
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)84995-3

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✦ Synopsis

The ratio of methylenecyclopentane to methylenecyclohexane derivatives observed in the vinyl radical cyclization increases with the concentration of substrate and tin hydride.

📜 SIMILAR VOLUMES

Six- versus five-membered ring formation

Six- versus five-membered ring formation in radical cyclization of 1-vinyl-5-methyl-5-hexenyl radicals

✍ Ana M. Gómez; Marı́a D. Company; Clara Uriel; Serafı́n Valverde; J.Cristóbal Lóp 📂 Article 📅 2002 🏛 Elsevier Science 🌐 French ⚖ 74 KB

Radical cyclization of 1-vinyl-5-methyl-5-hexenyl radicals (radical numbering) affords six-membered ring products prevailing over the isomeric five-membered ring compounds; the former are generated through two reaction pathways: 6-endo-trig ring closure and rearrangement of intermediate methylenecyc