TY - JOUR
T1 - Reactions of α,β-enones with diazo compounds
T2 - Part 3. On the nature of the 1,5-ring closure of α,β-enone ylides
AU - Anaç, Olcay
AU - Özdemir, Ayşe Daut
AU - Sezer, Özkan
PY - 2003
Y1 - 2003
N2 - Carbonyl ylides arising from ethyl acetodiazoacetate/dimethyl diazomalonate and α,β-enones with mainly s-cis conformations underwent disrotatory cyclization to produce dihydrofuran derivatives. This process proved to be sensitive to steric effects. The corresponding ylides arising from rather s-trans α,β-enals yielded dioxole derivatives. The mechanisms of the reactions are discussed.
AB - Carbonyl ylides arising from ethyl acetodiazoacetate/dimethyl diazomalonate and α,β-enones with mainly s-cis conformations underwent disrotatory cyclization to produce dihydrofuran derivatives. This process proved to be sensitive to steric effects. The corresponding ylides arising from rather s-trans α,β-enals yielded dioxole derivatives. The mechanisms of the reactions are discussed.
UR - http://www.scopus.com/inward/record.url?scp=0037233224&partnerID=8YFLogxK
U2 - 10.1002/hlca.200390030
DO - 10.1002/hlca.200390030
M3 - Article
AN - SCOPUS:0037233224
SN - 0018-019X
VL - 86
SP - 290
EP - 298
JO - Helvetica Chimica Acta
JF - Helvetica Chimica Acta
IS - 2
ER -