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Paper | Special issue | Vol 49, No. 1, 1998, pp.149-156
Published online, 1st January, 1970
DOI: 10.3987/COM-98-S10
Samarium Iodide Promoted Coupling of N-Substituted Azetidin-3-ones. A Novel Route to Spiroannulated Heterocyclic Oxiranes

Alan P. Marchand,* Arokiasamy Devasagayaraj, and Simon G. Bott*

*Department of Chemistry, University of North Texas, Denton, Texas 76203, U.S.A.


Samarium iodide promoted reductive coupling of N-ethoxycarbonylazetidine-3-one (1a), N-p-toluenesulfonylazetidine-3-one (1b), and N-benzhydrylazetidine-3-one (1c) each afforded the corresponding pinacol (2a-2c, respectively). Each pinacol was converted into the corresponding dimesylate (3a-3c, respectively). When heated in the presence of base, 3a and 3b each afforded the corresponding spirocyclic oxirane (4a and 4b, respectively). In contrast to the behavior of 3a and 3b,3c proved to be inert under these conditions. Structure 4b was established unequivocally via application of X-Ray crystallographic methods.