Rh2(OAc)4-Catalyzed Reactions of α,β-Conjugated Enon Compounds with 2-Diazo-5,5-Dimethyl-1,3-Cyclohexandione

Year 2024, Volume: 14 Issue: 1, 249 - 261, 15.03.2024

Füsun Şeyma Güngör , Ayşe Özdemir

https://doi.org/10.31466/kfbd.1393378

Abstract

Reactions of α,β-conjugated enone compounds, and 2-diazo-5,5-dimethyl-1,3-hexanedione were carried out under the dirhodium tetraacetate (Rh2(OAc)4) catalyst. The structures of the obtained products were characterized by FT-IR, GC-MS, 1H NMR, and 13C NMR methods. 6,6-Dimethyl-3,5,6,7-tetrahydro-4H-spiro[benzofuran-2,2'-bicyclo[2.2.1]heptane]-3',4-dione was obtained from the reaction of 3-methylidene-bicyclo[2.2.1]heptan-2-one, the first α,β-conjugated enone compound used in the study, as a single product. The second α,β-conjugated enone compound, 1-morpholinoprop-2-en-1-one, did not react with Rh-carbene, and only the carbene dimer was obtained from this reaction.

Keywords

Diazodicarbonyl, Conjuge Enone, Dihydrofuran, Rh2(OAc)4

Project Number

İTÜ-Bap proje ID-kod 9039-1819

α,β-Konjuge Enon Bileşiklerinin 2-Diazo-5,5-Dimetil-1,3-Sikloheksandion ile Rh2(OAc)4-Katalizli Tepkimeleri

Abstract

α,β-Konjuge enon bileşikleri ile 2-diazo-5,5-dimetil-1,3-heksandionun dirodyum tetraasetat (Rh2(OAc)4) katalizörlüğünde tepkimeleri gerçekleştirilmiştir. Elde edilen ürünlerin yapıları FT-IR, GC-MS ve 1H NMR ve 13C NMR yöntemleri ile karakterize edilmiştir. Çalışmada kullanılan ilk α,β-konjuge enon bileşiği olan 3-metiliden-bisiklo[2.2.1]heptan-2-onun tepkimesinden 6,6-dimetil-3,5,6,7-tetrahidro-4H-spiro[benzofuran-2,2’-bisiklo[2.2.1]heptan]-3’,4-dion bileşiği tek ürün olarak elde edilmiştir. İkinci α,β-konjuge enon bileşiği olan 1-morfolinoprop-2-en-1-on Rh-karbeni ile tepkime vermemiş olup bu tepkimeden sadece karben dimeri elde edilmiştir.

Keywords

Diazodikarbonil, Konjuge Enon, Dihidrofuran, Rh2(OAc)4

Ethical Statement

Yapılan çalışmada araştırma ve yayın etiğine uyulmuştur.

Supporting Institution

İ.T.Ü. Bilimsel Araştırmalar Proje Birimi

Project Number

İTÜ-Bap proje ID-kod 9039-1819

Thanks

Bu çalışma İ.T.Ü. Bilimsel Araştırmalar Proje Birimi tarafından (Proje no: İTÜ-Bap proje ID-kod 9039-1819) desteklenmiştir.

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