Abstract
The Kiliani reaction, i.e. the elongation of the carbon chain by means of cyanide addition to the carbonyl group of carbohydrate derivatives, is studied on lower C3-, C4- and C6-ketoses under continuous flow conditions. Depending on the process parameters, the corresponding cyanohydrins or α-hydroxycarboxylic acids are obtained. A simple on-line purification of the effluent is studied using cation exchange resins. Reactions provide high yields and selectivity within short residence times, emphasizing the assets of the continuous flow process versus the batch process.
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Yu, H.; Ballard, C.E.; Boyle, P.D.; Wang, B. Tetrahedron 2002, 58, 7663–7679.
Kiliani, H. Ber. Dtsch. Chem. Ges. 1885, 18, 3066–3072
Kiliani, H. Ber. Dtsch. Chem. Ges. 1886, 19, 221–227.
http://www.orgsyn.org. Accessed 4.10.2010.
Hotchkiss, D.J.; Soengas, R.; Simone, M.I.; van Ameijde, J.; Hunter, S.; Cowley, A.R.; Fleet, G.W.J. Tetrahedron Lett. 2004, 45, 9461–9464
Soengas, R.; Izumori, K.; Simone, M.I.; Watkin, D.J.; Skytte, U.P.; Soetaert, W.; Fleet, G.W.J. Tetrahedron Lett. 2004, 46, 5755–5759.
Wiles, C; Watts, P. Micro Reaction Technology in Organic Synthesis; CRC Press Taylor & Francis: Boca Raton, FL 2011; pp xxii+432.
Acke, D.R.J. Evaluation of Microreactor Technology for Multicomponent Reactions. Ph.D. thesis, Faculty of Bioscience Engineering, Ghent University, Ghent, 2007
Acke, D.R.J.; Orru, R.V.A.; Stevens, C.V. QSAR Comb. Sci. 2006, 25, 474–483
Acke, D.R.J.; Stevens, C.V. Green Chem. 2007, 9, 386–390
Acke, D.R.J.; Stevens, C.V.; Roman, B.I. Org. Process Res. Dev. 2008, 12, 921–928
Heugebaert, T.S.A.; Roman, B.I.; De Blieck, A.; Stevens, V. Tetrahedron Lett. 2010, 51, 4189–4191.
Monbaliu, J.C.M.R.; Cukalovic, A.; Marchand-Brynaert, J.; Stevens, C.V. Tetrahedron Lett. 2010, 51, 5830–5833
Monbaliu, J.C.M.R.; Winter, M.; Chevalier, B.; Schmidt, F.; Jiang, Y.; Hoogendoorn, R.; Kousemaker, M.A.; Stevens, C.V. Bioresource Technol. 2011, 102, 9304–9307.
Schwalbe, T.; Golbig K. et al. Eur. Pat. Appl. EP 1123734, 2001. Chem. Abstr. 2001, 135, 154468b.
http://www.thalesnano.com. Accessed 21.10.2011.
http://www.cyanidecode.org; Cummings, T. F. Occup. Med.-C 2004, 54, 82–85 (Safety measures). Accessed 21.10.2011.
Serianni, A.S.; Nunez, H.A.; Barker, R. J. Org. Chem. 1980, 45, 3329–3341.
Sukata, K. Buil. Chem. Soc. Jpn. 1987, 60, 3820–3822.
http://www.lancevalves.com. Accessed 2.10.2010.
Blazer, R.M.; Whaley, T.W. J. Am. Chem. Soc. 1980, 102, 5082–5085.
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Cukalovic, A., Monbaliu, JC.M., Heynderickx, G.J. et al. User Friendly and Flexible Kiliani Reaction on Ketoses Using Microreaction Technology. J Flow Chem 2, 43–46 (2012). https://doi.org/10.1556/JFC-D-12-00003
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DOI: https://doi.org/10.1556/JFC-D-12-00003