Carbonyl ylide reactions of α-benzylidene-β-dicarbonyl compounds: competitive formation of dihydrofurans and dihydrobenzoxepines

Olcay Anaç; Özkan Sezer; Özlem Candan; Füsun Şeyma Güngör; M. Şerif Cansever

doi:10.1016/j.tetlet.2007.11.197

Carbonyl ylide reactions of α-benzylidene-β-dicarbonyl compounds: competitive formation of dihydrofurans and dihydrobenzoxepines

Olcay Anaç^*
, Özkan Sezer
, Özlem Candan
, Füsun Şeyma Güngör
, M. Şerif Cansever

^*Corresponding author for this work

Department of Chemistry

Istanbul Technical University

Research output: Contribution to journal › Article › peer-review

29 Citations (Scopus)

Abstract

α-Benzylidene-β,β′-biscarbonyl compounds were reacted with dimethyl diazomalonate using Cu(II) acetylacetonate as a catalyst. Dihydrofurans or mixtures of dihydrofurans and dihydrobenzoxepines were obtained depending on the nature of the carbonyl group present in the starting material.

Original language	English
Pages (from-to)	1062-1065
Number of pages	4
Journal	Tetrahedron Letters
Volume	49
Issue number	6
DOIs	https://doi.org/10.1016/j.tetlet.2007.11.197
Publication status	Published - 4 Feb 2008

Keywords

1,5-Electrocyclization
1,7-Electrocyclization
Carbene
Dihydrobenzoxepine
Dihydrofuran

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10.1016/j.tetlet.2007.11.197

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title = "Carbonyl ylide reactions of α-benzylidene-β-dicarbonyl compounds: competitive formation of dihydrofurans and dihydrobenzoxepines",

abstract = "α-Benzylidene-β,β′-biscarbonyl compounds were reacted with dimethyl diazomalonate using Cu(II) acetylacetonate as a catalyst. Dihydrofurans or mixtures of dihydrofurans and dihydrobenzoxepines were obtained depending on the nature of the carbonyl group present in the starting material.",

keywords = "1,5-Electrocyclization, 1,7-Electrocyclization, Carbene, Dihydrobenzoxepine, Dihydrofuran",

author = "Olcay Ana{\c c} and {\"O}zkan Sezer and {\"O}zlem Candan and G{\"u}ng{\"o}r, \{F{\"u}sun {\c S}eyma\} and Cansever, \{M. {\c S}erif\}",

year = "2008",

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doi = "10.1016/j.tetlet.2007.11.197",

language = "English",

volume = "49",

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journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Carbonyl ylide reactions of α-benzylidene-β-dicarbonyl compounds

T2 - competitive formation of dihydrofurans and dihydrobenzoxepines

AU - Anaç, Olcay

AU - Sezer, Özkan

AU - Candan, Özlem

AU - Güngör, Füsun Şeyma

AU - Cansever, M. Şerif

PY - 2008/2/4

Y1 - 2008/2/4

N2 - α-Benzylidene-β,β′-biscarbonyl compounds were reacted with dimethyl diazomalonate using Cu(II) acetylacetonate as a catalyst. Dihydrofurans or mixtures of dihydrofurans and dihydrobenzoxepines were obtained depending on the nature of the carbonyl group present in the starting material.

AB - α-Benzylidene-β,β′-biscarbonyl compounds were reacted with dimethyl diazomalonate using Cu(II) acetylacetonate as a catalyst. Dihydrofurans or mixtures of dihydrofurans and dihydrobenzoxepines were obtained depending on the nature of the carbonyl group present in the starting material.

KW - 1,5-Electrocyclization

KW - 1,7-Electrocyclization

KW - Carbene

KW - Dihydrobenzoxepine

KW - Dihydrofuran

UR - https://www.scopus.com/pages/publications/37849035612

U2 - 10.1016/j.tetlet.2007.11.197

DO - 10.1016/j.tetlet.2007.11.197

M3 - Article

AN - SCOPUS:37849035612

SN - 0040-4039

VL - 49

SP - 1062

EP - 1065

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 6

ER -

Carbonyl ylide reactions of α-benzylidene-β-dicarbonyl compounds: competitive formation of dihydrofurans and dihydrobenzoxepines

Abstract

Keywords

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