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Communication | Special issue | Vol 70, No. 1, 2006, pp.87-91
Published online, 14th November, 2006
DOI: 10.3987/COM-06-S(W)22
The 1,3-Dipolar Cycloaddition of Methyl Acrylate to Hindered 3-Oxidopyraziniums

Madeleine Helliwell, Yun You, and John A. Joule*

*The School of Chemistry, The University of Manchester, Oxford Road, Manchester, M13 9PL, U.K.


Methyl acrylate adds to 1,2,5,6-tetramethyl-3-oxidopyrazinium to give a standard 1,3-dipolar cycloadduct — a 3,8-diazabicyclo[3.2.1]octan-2-one — however from the more hindered 5,6-diethyl-1,2-dimethyl-3-oxidopyrazinium, a 4,7-dioxo-3,6-diazabicyclo[3.2.1]octane, the result of extensive rearrangement of the initial 1,3-dipolar cycloadduct, was obtained and its structure determined by X-Ray crystallographic analysis.