Synthesis and reactivity of a novel group of hydroxylamine-containing 2π-and 4π-components

…, DS Walter, CS Frampton, T Gallagher

Index: Pearce, Alan J.; Walter, Daryl S.; Frampton, Christopher S.; Gallagher, Timothy Journal of the Chemical Society - Perkin Transactions 1, 1998 , # 5 p. 847 - 852

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Abstract

The synthesis of hydroxylamine-based reagents, alkene 2, alkyne 3 and a butadienyl variant pyrone 4 are described. While the relative instability of alkyne 3 has limited further evaluation, alkene 2 and pyrone 4 successfully participate in 1, 3-dipolar and Diels–Alder cycloaddition reactions respectively. Reaction of 4 with DMAD gives O-arylated hydroxylamine 13, the structure of which is confirmed by crystallographic analysis.