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

Yıl 2024, Cilt: 14 Sayı: 1, 249 - 261, 15.03.2024

Füsun Şeyma Güngör Ayşe Özdemir

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

Öz

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.

Anahtar Kelimeler

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

Proje Numarası

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

Öz

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.

Anahtar Kelimeler

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

Etik Beyan

Yapılan çalışmada araştırma ve yayın etiğine uyulmuştur.

Destekleyen Kurum

İ.T.Ü. Bilimsel Araştırmalar Proje Birimi

Proje Numarası

İTÜ-Bap proje ID-kod 9039-1819

Teşekkür

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

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