The first preparation of beta-lactones by radical cyclization

Castle, K., Hau, C.S., Sweeney, J.B. and Tindall, C. (2003) The first preparation of beta-lactones by radical cyclization. Organic Letters, 5 (5). pp. 757-759. ISSN 1523-7060 doi: 10.1021/ol0340235

Abstract/Summary

beta-Lactones have, for the first time, been prepared by 4-exo-trig radical cyclization. Thus, alpha-ethenoyloxy radicals react in the presence of tributylstannane in a photothermal process to give beta-lactones. Highest yields were obtained when groups capable of stabilizing a carboncentered radical were present at the 3-position of the alkenoate acceptor.