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Divergent reactivity of phenol- and anisole-tethered donor-acceptor α-diazoketones

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JournalTetrahedron
DateAccepted/In press - 25 Jan 2018
DateE-pub ahead of print (current) - 3 Feb 2018
Early online date3/02/18
Original languageEnglish

Abstract

The first study of the divergent reactivity of phenol/anisole-tethered donor-acceptor α-diazoketones is described. Four distinct product classes were shown to be accessible from closely related α-diazoketone precursors, with the reaction outcome dependent on the nature of the oxygen substituent on the phenol/anisole ring and the catalyst used to decompose the diazo group. Anisole and TBS-protected derivatives selectively produce three products types (cyclopropanes, tetralones and 1,2-dicarbonyls) while phenols selectively produce spirocyclic dienones.

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© Elsevier, 2018. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy.

    Research areas

  • Anisole, Buchner reaction, Divergent reactivity, Phenol, α-Diazocarbonyl compounds

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