J. Vecht, R. Spoor, H. Steinberg
Sep 2, 2010
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Journal
Recueil des Travaux Chimiques des Pays-Bas
Abstract
Cyclopropanes 1b, 1c and 1d, carrying an o-hydroxyphenyl group as a proton donor and - at the same small ring carbon atom - a potential proton acceptor X = NMe2, OMe or SMe, have been thermolysed. Between 350° and 600° cyclopropyl-ring opening takes place with isomerization to substituted (o-hydroxyphenyl)propenes 8b, 8c and (mainly) 8d, each of which can be hydrolysed to o-hydroxypropiophenone 2. Only when X = SMe, does protonation on sulfur lead to formal MeSH elimination. A similar reaction is also found when X = Me3N⊕, thus sharply contrasting with X = Me2NH⊕.