First direct evidence of radical intermediates in samarium diiodide induced cyclization by ESR spectra.

Masakazu Sono, Shin-ichi Hanamura, Midori Furumaki, Hisao Murai, Motoo Tori

Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Tokushima 770-8514, Japan. sono@ph.bunri-u.ac.jp

Organic letters 2011 Nov 4

filter terms:

The mechanism of samarium diiodide (SmI(2))-induced cyclization of α,β-unsaturated esters and ketones to bicyclic compounds was examined using ESR spectroscopy. This is the first report of direct evidence of the radical intermediates in the SmI(2) reaction. The preferential reduction of the α,β-unsaturated carbonyl part in some substrates should be recognized as a main route. © 2011 American Chemical Society

Citation

Masakazu Sono, Shin-ichi Hanamura, Midori Furumaki, Hisao Murai, Motoo Tori. First direct evidence of radical intermediates in samarium diiodide induced cyclization by ESR spectra. Organic letters. 2011 Nov 4;13(21):5720-3