The Reactions of a-Ylidene (Vinylidene, Benzylidene, Styrylmethylidene) Bis[carbonyls] with Copper Mono/Bis[carbonylcarbenoids]

Merey G., Kaya M., Anac O.

HELVETICA CHIMICA ACTA, cilt.95, sa.8, ss.1409-1424, 2012 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 95 Sayı: 8
  • Basım Tarihi: 2012
  • Doi Numarası: 10.1002/hlca.201200004
  • Dergi Adı: HELVETICA CHIMICA ACTA
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.1409-1424
  • Anahtar Kelimeler: Electrocyclic reactions, Furan, dihydro-, Diazo compounds, Carbenoid intermediates, Benzoxepine, dihydro-, C-H FUNCTIONALIZATION, ASYMMETRIC 4+3 CYCLOADDITIONS, DIAZO-COMPOUNDS, CYCLIC ETHERS, ORGANOCATALYTIC CYCLOPROPANATION, STEREOSELECTIVE-SYNTHESIS, DIHYDROFURAN DERIVATIVES, DIMETHYL DIAZOMALONATE, DICARBONYL-COMPOUNDS, CARBONYL-YLIDES
  • Marmara Üniversitesi Adresli: Hayır

Özet

The [Cu(acac)2]-catalyzed reactions of various alpha,beta,gamma,delta-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.