Microwave Assisted and Montmorillonite-K10 Catalyzed Alcohollysis of Benzonorbornadiene Oxide: Synthesis of Regioselective New Alkoxy Alcohols by Wagner–Meerwein Rearrangement

Abstract

In this study, microwave assisted ring opening of benzonorbornadiene epoxide with alcohols was investigated. New alkoxy alcohols were synthesized regioselectively by Wagner–Meerwein rearrangement in short reaction times (up to 10 minutes) with high yield in the presence of a cheap and environmentally friendly heterogeneous montmorillonite-K10 catalyst. The products were purified by filtration only.

Keywords

• Benzonorbornadiene oxide
• alkoxy alcohol
• montmorillonite-K10
• Wagner–Meerwein rearrangement
• microwave

Benzonorbornadien Oksit’in Mikrodalga Destekli ve Montmorillonite-K10 Katalizli Alkolizi: Wagner–Meerwein Düzenlenmesi ile Regioseçici Yeni Alkoksi Alkollerin Sentezi

Abstract

Bu çalışmada, benzonorbornadien epoksitinin alkollerle mikrodalga destekli halka açılma tepkimeleri incelendi. Ucuz ve çevreci heterojen montmorillonite-K10 katalizörü eşliğinde yüksek verim ile kısa reaksiyon süresinde (10 dakikaya kadar) Wagner–Meerwein düzenlenmesi ile regioseçici olarak yeni alkoksi alkoller sentezlendi. Ürünler sadece süzme ile saflaştırıldı.

Keywords

• Benzonorbornadien oksit
• alkoksi alkol
• montmorillonite-K10
• Wagner–Meerwein düzenlenmesi
• mikrodalga

Thanks

Bu çalışmaya katkılarından dolayı, Atatürk Üniversitesi Fen Fakültesi Kimya Bölümü’ne teşekkür ederiz.

References

1. Arrowsmith JE, Campbell SF, Cross PE, Stubbs JK, Burges RA, Gardiner DG, Blackburn KJ, 1986. Long-acting dihydropyridine calcium antagonists. 1. 2-Alkoxymethyl derivatives incorporating basic substituents. Journal of medicinal chemistry, 29 (9): 1696-1702.
2. Barluenga J, Vázquez-Villa H, Ballesteros A, González JM, 2002. Copper (II) tetrafluoroborate catalyzed ring-opening reaction of epoxides with alcohols at room temperature. Organic Letters, 4 (17), 2817-2819.
3. Barreca D, Copley MP, Graham AE, Holmes JD, Morris MA, Seraglia R, Tondello E, 2006. Methanolysis of styrene oxide catalysed by a highly efficient zirconium-doped mesoporous silica. Applied Catalysis A: General, 304, 14-20.
4. Bhuyan D, Saikia L, Dutta DK, 2014. Modified Montmorillonite clay catalyzed regioselective ring opening of epoxide with amines and alcohols under solvent free conditions. Applied Catalysis A: General, 487, 195-201.
5. Bonini C, Righi G, 1994. Regio-and chemoselective synthesis of halohydrins by cleavage of oxiranes with metal halides. Synthesis, 1994 (03): 225-238.
6. Cao L, Lee J, Chen W, Wood TK, 2006. Enantioconvergent production of (R)‐1‐phenyl‐1, 2‐ethanediol from styrene oxide by combining the Solanum tuberosum and an evolved Agrobacterium radiobacter AD1 epoxide hydrolases. Biotechnology and bioengineering, 94 (3): 522-529.
7. Ch Ghosh K, Banerjee I, Sinha S, 2018. Montmorillonite K10 catalyzed highly regioselective azidolysis of epoxides: A short and efficient synthesis of phenylglycine. Synthetic Communications, 48 (22): 2923-2934.
8. Dastan A, 1995. Hidrokarbonların Yüksek Sıcaklık Brominasyonu, Atatürk Üniversitesi Fen Bilimleri Enstitüsü, Doktora Tezi (Basılmış).

9. Dastan A, Demir U, Balci M, 1994. Functionalization of benzonorbornadiene: high-temperature bromination and electrochemical oxidation. The Journal of Organic Chemistry, 59 (22): 6534-6538.
10. Demir E, Sari O, Çetinkaya Y, Atmaca U, Erdem SS, Çelik M, 2020. One-pot synthesis of oxazolidinones and five-membered cyclic carbonates from epoxides and chlorosulfonyl isocyanate: theoretical evidence for an asynchronous concerted pathway. Beilstein journal of organic chemistry, 16 (1): 1805-1819.
11. Dutta P, Kalita P, Baruah PK, 2016. Room temperature ring opening of epoxides over triflic acid functionalized cage like mesoporous materials. ChemistrySelect, 1 (8): 1650-1657.
12. Hermann K, Nakhla M, Gallucci J, Dalkilic E, Dastan A, Badjić JD, 2013. A molecular claw: a dynamic cavitand host. Angewandte Chemie, 125 (43): 11523-11526.
13. Iranpoor N, Tarrian T, Movahedi Z, 1996. FeCl3• 6H2O supported on SiO2 catalysed ring opening of epoxides with alcohols, acetic Acid, water, chloride, bromide and nitrate ions. Synthesis, 1996 (12): 1473-1476.
14. Iranpoor N, Zeynizadeh B, 1999. TiCl3(OTf) and TiO(TFA)2 Efficient catalysts for ring opening of epoxides with alcohols, acetic acid and water. Synthetic communications, 29 (6): 1017-1024.
15. Khan R, Chen J, Fan B, 2020. Versatile Catalytic Reactions of Norbornadiene Derivatives with Alkynes. Advanced Synthesis & Catalysis, 362 (8): 1564-1601.
16. Kino T, Hatanaka H, Hashimoto M, Nishiyama M, Goto T, Okuhara M, Imanaka H, 1987. FK-506, a novel immunosuppressant isolated from a Streptomyces I. Fermentation, isolation, and physico-chemical and biological characteristics. The Journal of antibiotics, 40 (9): 1249-1255.
17. Kocak R, Akın ET, Kalın P, Talaz O, Saracoglu N, Dastan A, Durdagi S, 2016. Synthesis of some novel norbornene‐fused pyridazines as potent inhibitors of carbonic anhydrase and acetylcholinesterase. Journal of heterocyclic chemistry, 53 (6): 2049-2056.
18. Kocak R, Borsato G, De Lucchi O, Daştan A, 2014. Norbornanoid chiral ketones by desymmetrization of dibromoalkenes. Helvetica Chimica Acta, 97 (4): 537-545.
19. Kureshy RI, Agrawal S, Kumar M, Khan NUH, Abdi SH, Bajaj HC, 2010. Hβ zeolite: An efficient and reusable catalyst for ring-opening of epoxides with amines under microwave irradiation. Catalysis letters, 134 (3): 318-323.
20. Li Y, Tan Y, Herdtweck E, Cokoja M, Kühn FE, 2010. Synthesis of nitrile coordinated Lewis acids Al(OC(CF3)2R)3 and their application in catalytic epoxide ring-opening reactions. Applied Catalysis A: General, 384 (1-2): 171-176.
21. Likhar PR, Kumar MP, Bandyopadhyay AK, 2001. Ytterbium trifluoromethanesulfonate Yb (OTf)3: an efficient, reusable catalyst for highly selective formation of β-alkoxy alcohols via ring-opening of 1, 2-epoxides with alcohols. Synlett, 2001 (06): 0836-0838.
22. Liu YH, Liu QS, Zhang ZH, 2009. An efficient Friedel–Crafts alkylation of nitrogen heterocycles catalyzed by antimony trichloride/montmorillonite K-10. Tetrahedron Letters, 50 (8): 916-921.
23. Nişancı B, Dalkılıç E, Güney M, Daştan A, 2009. Synthesis and Diels–Alder cycloaddition reaction of norbornadiene and benzonorbornadiene dimers. Beilstein Journal of Organic Chemistry, 5 (1): 39.
24. Rahmatpour A, Sajjadinezhad SM, 2021. Cross‐linked poly (N‐vinylpyrrolidone)‐titanium tetrachloride complex: A novel stable solid TiCl4 equivalent as a recyclable polymeric Lewis acid catalyst for regioselective ring‐opening alcoholysis of epoxides. Applied Organometallic Chemistry, 35 (11): e6385.
25. Robinson MW, Buckle R, Mabbett I, Grant GM, Graham AE, 2007. Mesoporous aluminosilicate promoted alcoholysis of epoxides. Tetrahedron letters, 48 (27): 4723-4725.
26. Salehi P, Khodaei MM, Zolfigol MA, Keyvan A, 2003. Magnesium hydrogensulfate: a cheap and efficient catalyst for the conversion of epoxides into β-alkoxy alcohols, vicinal-diols, and thiiranes. Synthetic communications, 33 (17): 3041-3048.
27. Sonawane HR, Sethi SC, Merchant SN, 1984. Photo-induced reactions of some epoxides in isopropanol: effect of structural parameters on photoreduction and photosolvolysis. Indian Journal of Chemistry, 23B, 934-939.
28. Tangestaninejad S, Moghadam M, Mirkhani V, Yadollahi B, Mirmohammadi SMR, 2006. Mild and efficient ring opening of epoxides catalyzed by potassium dodecatungstocobaltate (III). Monatshefte für Chemie/Chemical Monthly, 137 (2): 235-242.
29. Vilotijevic I, Jamison TF, 2009. Epoxide‐opening cascades in the synthesis of polycyclic polyether natural products. Angewandte Chemie International Edition, 48(29), 5250-5281.
30. Wallis PJ, Gates WP, Patti AF, Scott JL, Teoh E, 2007. Assessing and improving the catalytic activity of K-10 montmorillonite. Green Chemistry, 9 (9): 980-986.
31. Williams DBG, Lawton M, 2005. Aluminium triflate: a remarkable Lewis acid catalyst for the ring opening of epoxides by alcohols. Organic & biomolecular chemistry, 3 (18): 3269-3272.
32. Yan Z, Tian J, Wang K, Nigam KD, Luo G, 2021. Microreaction processes for synthesis and utilization of epoxides: A review. Chemical Engineering Science, 229, 116071.
33. Yarapathi RV, Reddy SM, Tammishetti S, 2005. Polymer supported ferric chloride: Regiospecific nucleophilic ring opening of epoxides. Reactive and Functional Polymers, 64 (3): 157-161.
34. Zuo H, Li ZB, Zhao BX, Miao JY, Meng LJ, Jang KW, Shin DS, 2011. Highly efficient microwave-assisted aminolysis of epoxides in water. Bulletin of the Korean Chemical Society, 32(spc8), 2965-2969.