3-Vinyl-2,5-dihydrothiophene 1,1-dioxide: a novel, easily accessible, high-yielding precursor to [3]dendralene, the simplest representative of the diene-transmissive polyenes
- 1 January 1991
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 2,p. 114-115
- https://doi.org/10.1039/c39910000114
Abstract
Cheleotropic extrusion of SO2 from readily prepared 3-vinyl-2,5-dihydrothiophene 1,1-dioxide 2 provides a clean and efficient route to [3]dendralene (3-methylenepenta-1,4-diene 1), the simplest member of the diene-transmissive polyenes, which contrary to previous reports is a stable, easily handled compound that shows unexpected selectivity in Diels–Alder cycloadditions, thus enhancing its utility as a tandem annelating reagent.Keywords
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