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Communication | Special issue | Vol 25, No. 1, 1987, pp.13-17
Published online, 1st January, 1970
DOI: 10.3987/S-1987-01-0013
Reaction of Pyridine 1-Oxide with Methyl Propiolate: A Pyrido-oxepine and Other Novel Products

Rudolph A. Abramovitch, Dharma Kishore, Marek Konieczny, and Zbigniew Dauter

*Department of Chemistry, Clemson University, Clemson, SC 29631, U.S.A.


The title reaction is much more complex than those of pyridine 1- oxides with other activated acetylenes. Eight products have been isolated and five characterized: 4-8. The most interesting is a pyrido-oxepin 8 whose structure has been firmly established by single crystal X-ray analysis The main products thus result from reaction of 3 moles of methyl propiolate with one mole of pyridine 1-oxide. The 1:1 (6) and 1:2 (7) adducts are very minor products.