The reactions of α-ylidene (vinylidene, benzylidene, styrylmethylidene) bis[carbonyls] with copper mono/bis[carbonylcarbenoids]

Gökçe Merey*, Mustafa Kaya, Olcay Anaç

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

8 Citations (Scopus)

Abstract

The [Cu(acac) 2]-catalyzed reactions of various α,β,γ,δ-unsaturated bis-ketones/bis-esters/bis-keto esters with dimethyl diazomalonate and ethyl diazoacetate were studied. Total steric/electronic convenience of the present reaction paths was investigated. Methoxy/nitro substituents in m-/p-positions on benzylidene biscarbonyls did not alter the general routes of the reactions, supporting concerted mechanism. Dihydrobenzoxepine/oxepine formation was sterically sensitive to the related pre-ring conformation, and dihydrofurans were effected by both charge control and steric factors.

Original languageEnglish
Pages (from-to)1409-1424
Number of pages16
JournalHelvetica Chimica Acta
Volume95
Issue number8
DOIs
Publication statusPublished - Aug 2012

Keywords

  • Benzoxepine, dihydro-
  • Carbenoid intermediates
  • Diazo compounds
  • Electrocyclic reactions
  • Furan, dihydro-

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