Radical cyclizations of bromo acylsilanes and intramolecular trapping of the rearranged α-silyloxy radicals

✍ Scribed by Yeun-Min Tsai; Kuo-Hsiang Tang; Weir-Torn Jiaang

• Publisher: Elsevier Science
• Year: 1993
• Tongue: French
• Weight: 261 KB
• Volume: 34
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)91780-5

✦ Synopsis

Radical 1.5e.w cyclizations of acylsilanes involving secondary radicals am quite effective. In contrast, 1.6~~ cycliiions are more. sensitive toward steric effect. Tandem radical cycliioa process can be designed.

Recently we reported a novel reaction involving addition of primary radicals to the carbonyl of acylsilanesl2 (Scheme I). The resulting oxygen radical undergoes a possibly irreversible radical Brook rearrangement3 followed by hydrogen abstraction to give cyclopentyl silyl ether. In order to extend the