TY - JOUR
T1 - The reactions of α-ylidene (vinylidene, benzylidene, styrylmethylidene) bis[carbonyls] with copper mono/bis[carbonylcarbenoids]
AU - Merey, Gökçe
AU - Kaya, Mustafa
AU - Anaç, Olcay
PY - 2012/8
Y1 - 2012/8
N2 - 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.
AB - 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.
KW - Benzoxepine, dihydro-
KW - Carbenoid intermediates
KW - Diazo compounds
KW - Electrocyclic reactions
KW - Furan, dihydro-
UR - http://www.scopus.com/inward/record.url?scp=84865328483&partnerID=8YFLogxK
U2 - 10.1002/hlca.201200004
DO - 10.1002/hlca.201200004
M3 - Article
AN - SCOPUS:84865328483
SN - 0018-019X
VL - 95
SP - 1409
EP - 1424
JO - Helvetica Chimica Acta
JF - Helvetica Chimica Acta
IS - 8
ER -