Reduction Of Α,Β-Unsaturated Carbonyl Compounds And Strained Alkenes Under Mild Conditions

Öz

Birch reductions of two acids, an ester and a chalcone compounds, which are α,β-unsaturated carbonyl compounds, were investigated under different conditions. Birch reductions of norbornadiene and benzonorbornadiene compounds containing strained isolated double bonds were also investigated under different conditions.

Anahtar Kelimeler

• Birch reduction
• lithium
• gas ammonium
• α
• β-unsaturated compounds
• strained

Proje Numarası

Proje No: FDK-2018-6671

α,β-Doymamış Karbonil Bileşiklerin ve Gerilimli Alkenlerin Ilıman Şartlarda İndirgenmesi

Öz

α,β-Doymamış karbonil bileşikleri olan iki asit, bir ester ve bir kalkon bileşikleri farklı şartlarda Birch indirgemeleri incelendi. Ayrıca, gerilimli izole çift bağlar içeren norbornadien ve benzonorbornadien bileşiklerinin de farklı şartlarda Birch indirgemeleri incelendi.

Anahtar Kelimeler

• Birch indirgenmesi
• gaz amonyak
• doymamış karbonil bileşikleri
• gerilimli bileşikler
• Lityum

Destekleyen Kurum

Erzurum Atatürk Üniversitesi Fen Fakültesi Kimya Bölümünde gerçekleştirilmiştir. Çalışma Bilimsel Araştırma Projesi (Proje No: FDK-2018-6671) kapsamında olup Atatürk Üni. BAP tarafından desteklenmiştir. finansal ve lojistik açıdan destek sağlayan kurumlara, desteklerinden dolayı teşekkür ederiz.

Proje Numarası

Proje No: FDK-2018-6671

Etik Beyan

Etik Kurul kararı gerektiren bir durum yoktur

Teşekkür

Çalışmaya Bilimsel Araştırma Projesi (Proje No: FDK-2018-6671) kapsamında finansal ve lojistik açıdan destek sağlayan kurumlara, desteklerinden dolayı teşekkür ederiz.

Kaynakça

1. [1] H.O. House, “Modern synthetic reactions”, (1972), 2nd ed., W. A Benjamin, Los Angles, CA, pp 1-227.
2. [2] C.B. Wooster, L. Kenneth, K.L. Godfrey, “Mechanism of the reduction of unsaturated compounds with alkali metals and water”, Journal of the American Chemical Society, (1937), 59, 1615-1619.
3. [3] M.A. Yavari, “Doktora tezi (α,β- doymamış karbonil bileşiklerinin ılıman şartlarda Birch indirgenmesi ve norbornen türevi bileşiklerin 1,3-dipolar siklokatılması)”, Atatürk üniversitesi, Fen bilimleri enstitüsü, (2020).
4. [4] A.J. Birch, “Reduction by dissolving metals. part I”, Journal of the Chemical Society, (1944), 430-436.
5. [5] A. Menzek,“A new approach to understanding oxidation-reduction of compounds in organic chemistry”, Journal of Chemical Education, (2002), 79, 700-702.
6. [6] N. Balcı, L. Kelebekli, S. Göksu, B. Anıl, E. Şahin, “Synthesis and characterisation of 2,3a,5,6,7a-pentaacetoxy-octahydro-1H-indene from indan-2-ol”, Journal of Chemical Research, (2009), 248-251.
7. [7] E.S. Cook, A.J. Hill, “Local anesthetics derived from tetrahydronaphthalene. I. Esters of 2-dialkylamino-3-hydroxy-1,2,3,4-tetrahydronaphthalenes1”, Journal of the American Chemical Society, (1940), 62, 1995.
8. [8] A. Menzek, A. Altundaş, D. Gültekin, “A new, safe and convenient procedure for reduction of naphthalene and anthracene: Synthesis of tetraline by one-pot reaction”, Journal of Chemical Research, (2003), 752-753

9. [9] A. Altundaş, A. Menzek, D. Gültekin, M. Karakaya, “Excellent and convenient procedures for reduction of benzene and its derivatives”, Turkish Journal of Chemistry, (2005), 29, 513-518.
10. [10] A. Menzek, M.G. Karakaya, A.A. Kaya, “Reductions of benzene derivatives whose benzylic positions bear oxygen atoms under mild conditions”, Helvetica Chimica Acta, (2008), 91, 2299-230.
11. [11] T. Artunç, Y. Çetinkaya, H. Göçer, İ. Gülçin, A. Menzek, E. Şahin, C.T. Supuran, “Synthesis of 4-[2-(3,4-dimethoxybenzyl)cyclopentyl]-1,2-dimethoxybenzene derivatives and evaluations of their carbonic anhydrase isoenzymes inhibitory effects”, Chemical Biology And Drug Design, (2016), 87, 594–607.
12. [12] C. Bayrak, A. Menzek, M. Sevim, “Monodisperse NiPd alloy nanoparticles decorated on mesoporous graphitic carbon nitride as a catalyst for the highly efficient chemoselective reduction of α,β-unsaturated ketone compounds”, New Journal of Chemistry, (2020), 44, 13606.
13. [13] M. Sevim, C. Bayrak, A. Menzek, “Chemoselective reduction of α,β-unsaturated carbonyl compounds in the presence of CuPd alloy nanoparticles decorated on mesoporous graphitic carbon nitride as highly efficient catalyst”, Journal of Organometallic Chemistry (2022), 958, 122181.
14. [14] W.T. Borden, “Pyramidalized alkenes”, Chemical Reviews, (1989), 89, 5, 1095–1109.
15. [15] L.A. Paquette, C.C. Shen, “Isodicyclopentadienes and related molecules. 49. Synthesis, static structure, and kinetic stability of a syn-sesquinorbornatriene”, Journal of the American Chemical Society, (1990), 112, 1159-1164.
16. [16] A. Menzek, L. Kelebekli, A. Altundaş, E. Şahin F. Polat, “Cycloaddition reaction of 1,4-dihydronaphthalene 1,4-epoxide with cyclooctatetraene: Cope rearrangement in an adduct”, Helvetica Chimica Acta, (2008), 91, 2367-2378.
17. [17] M.A. Yavari, Y. Adiloğlu, R. Sağlamtaş, A.Tutar, İ. Gülçin, A. Menzek,“Synthesis and some enzyme inhibition effects of isoxazoline and pyrazoline derivatives including benzonorbornene unit”, Journal of Biochemical and Molecular Toxicology, (2022), 36, e22952.
18. [18] A. Menzek, N. Saraçoğlu, M. Kraweic, W.H. Watson, M. Balcı, “Synthesis of a new system containing pyramidalized double bond: cis-dicarbomethoxy-dihydroheptalene and its reaction with benzyne.”, Journal of Organic Chemistry, (1995), 60, 829-832.
19. [19] C. Bayrak, A. Menzek, “The first synthesis of phenylpropanoid derivative bromophenols including natural products: Formation of an indene derivative compound”, Tetrahedron, (2020), 76, 131016.