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The Reactions of α ‐Ylidene (Vinylidene, Benzylidene, Styrylmethylidene) Bis[carbonyls] with Copper Mono/Bis[carbonylcarbenoids]
Author(s) -
Merey Gökçe,
Kaya Mustafa,
Anaç Olcay
Publication year - 2012
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201200004
Subject(s) - chemistry , steric effects , ethyl diazoacetate , medicinal chemistry , electronic effect , copper , ring (chemistry) , nitro , catalysis , stereochemistry , organic chemistry , cyclopropanation , alkyl
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.