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Paper | Special issue | Vol 40, No. 1, 1995, pp.223-230
Published online, 1st January, 1970
DOI: 10.3987/COM-94-S12
Studies of Schmidt-Type Rearrangements of Pentacyclo[,6.03,10.05,9]undecan-8-one. Unexpected Incursion of the Huisgen Rearrangement

Alan P. Marchand*, Viktor D. Sorokin, D. Rajagopal, and Simon G. Bott

*Department of Chemistry, University of North Texas, NT Station, P.O. Box 305070, Denton, TX 76203-0068, U.S.A.


Reaction of pentacyclo[,]undecan-8-one (1) with H2NOSO3H-HCO2H affords two pentacyclic lactams (2a) (15%) and (2b) (30%). Reaction of 1 with HN3-Tf2O results in the formation of a pentacyclic urea (3) (16%) and a tricyclic azidonitrile (4) (18%). The unusual “double Schmidt rearrangement” that results in the formation of 3 is rationalized via formation of an intermediate tetrazole (5) which undergoes subsequent acylation with concomitant Huisgen rearrangement.