On the question of reversibility in the intramolecular addition of radicals to aldehydes to form cycloalkanols

✍ Scribed by Bert Fraser-Reid; Gregory D. Vite; Bik-Wah Anissa Yeung; Ray Tsang

• Publisher: Elsevier Science
• Year: 1988
• Tongue: French
• Weight: 205 KB
• Volume: 29
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)82007-9

✦ Synopsis

Experiments with two pairs of epimeric alcohols establish conclusively that the intramolecular aa%tlon of a primary radical to an aldehyde to give a cycloalkanoxyl radical is not a reversible process,

Recent publications from this laboratory have shown that radical cyclization of aldehydes is frequently a highly efficient reaction which can, in some circumstances, compete with ring closure of a 5-hexenyl radical. 1,2,3 Th us, for a system such as 1, a cyclohexanol(3, n = 6) was formed predominantly (and often exclusively) even when a methylcyclopentane (5, m = 5) was a plausible alternative.