Mechanism of the addition of tributyltin iodoacetate to alkenes

✍ Scribed by M. Degueil-Castaing; B. Oe Jeso; G.A. Kraus; K. Landgrebe; B. Maillard

• Book ID: 104219442
• Publisher: Elsevier Science
• Year: 1986
• Tongue: French
• Weight: 183 KB
• Volume: 27
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)85364-2

✦ Synopsis

The mechanism of the formation of lactones by free radical additions of tri-nbutyltin iodoacetate to alkenes occurs through a two-step process: a homolytic addition of the ester (addition of 'CH2-C02SnBu3, iodine transfer), followed by a fast ionic cyclization with elimination of tri-n-butyltin iodide.

The synthesis of y-butyrolactones by free radical processes is an active research area.

HeibaI initiated it using the manganic triacetate additions of acids to alkenes. Recently,