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Synthesis of 1-Aza-8-thiabicyclo[4.2.1]nona-2,4-diene 8,8-Dioxide and Its Conversion to a Strained Spirocycle via Photoinduced SO2−N Bond Cleavage

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journal contribution
posted on 15.04.2004, 00:00 by Leo A. Paquette, William R. S. Barton, Judith C. Gallucci
A route to the doubly unsaturated bridgehead sultam 12 has been developed. When irradiated at 350 nm, this conjugated diene is isomerized via a two-photon process to the structurally novel spiro heterocycle 17 constituted of cyclobutene, thietane dioxide, and pyrrolidine rings. A probable mechanism for the generation of 17 and select reactions thereof are reported.