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Silica‐Bound 3‐{2‐[Poly(ethylene Glycol)]ethyl}‐Substituted 1‐Methyl‐1H‐imidazol‐3‐ium Bromide: A Recoverable Phase‐Transfer Catalyst for Smooth and Regioselective Conversion of Oxiranes to β‐Hydroxynitriles in Water |
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| Authors: | Ali Reza?Kiasat Neda Ayashi Mehdi Fallah‐Mehrjardi |
| Institution: | 1. Chemistry Department, College of Science, Shahid Chamran University, P.O. Box 61357‐4‐3169, Ahvaz, Iran (phone: +98‐9163017427;2. fax: +98‐611‐3738044);3. Marine Chemistry Department, Khoramshahr University of Marine Science and Technology, Khoramshahr, Iran |
| Abstract: | A series of β‐hydroxynitriles were efficiently synthesized from the regioselective ring opening of oxiranes by cyanide anion in the presence of silica‐bound 3‐{2‐poly(ethylene glycol)]ethyl}‐substituted 1‐methyl‐1H‐imidazol‐3‐ium bromide (SiO2? PEG? ImBr) as a novel recoverable phase‐transfer catalyst in H2O (Scheme 1 and Table 2). The workup procedure was straightforward, and the catalyst could be reused over four times with almost no loss of catalytic activity and selectivity. |
| Keywords: | Nitriles β ‐hydroxy‐ Ring opening Oxiranes Epoxides Phase‐transfer catalysis Catalysis |