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Paper | Special issue | Vol 47, No. 1, 1998, pp.271-276
Published online, 1st January, 1970
DOI: 10.3987/COM-97-S(N)11
Synthesis of Isomeric Cage-functionalized Diacylfuroxans and Their Subsequent Thermolytic Fission to an Acyl Nitrile Oxide

Alan P. Marchand,* G. V. M. Sharma, Rajesh Shukla, and Simon G. Bott

*Department of Chemistry, University of North Texas, NT Station, P.O. Box 305070, Denton, TX 76203-5070, U.S.A.


A three step synthesis of a mixture of isomeric cage-functionalized furoxans (4) is described. When heated in the presence of ethyl propiolate, furoxans (4) undergo cycloreversion to afford two equivalents of the corresponding acyl nitrile oxide (5) which is trapped in situ by ethyl propiolate. The trapping reaction proceeds via a highly regioselective [3 + 2] cycloaddition to produce 6 (61% yyrld), whose structure was established unequivocally via application of X-Ray crystallographic methods. The observed regioselectivity of the [3 + 2] cycloaddition process is rationalized via frontier molecular orbital analysis by using semiempirical MO calculations (AM1 Hamiltonian) and at the HF/3-21G* level of theory.