Nucleophilic ring opening of 1,2-epoxides in aqueous medium

Issue in Honor of Prof. Domenico Spinelli ARKIVOC 2002 (xi) 293-311 Table 10. Lewis acid-catalyzed azidolysis in water of a,ß-epoxycarboxylic acids at pH 4.0 COOH COOH a COOH N3 OHNaN3, H2O O+ ß N3 OH (C-ß) (C-a) Epoxide Catalyst (mol%) T (°C) t (h) Ca (%) (C-ß)/(C-a) none 30 16 25 1 COOH Cu(NO3)2 (10) 30 16 >99 >99 O AlCl3 (1) 30 3.5 >99 >99 Me InCl3 (1) 30 10 >99 >99 none 65 24 82 0.8 COOH Cu(NO3)2 (10) 30 18 >99 >99 O n-Pr AlCl3 (1) 65 1.5 >99 >99 InCl3 (1) 65 2 >99 >99 none 30 3 13 >99 COOH O Cu(NO3)2 (10) 30 3 >99 >99 Me AlCl3 (1) 30 0.6 >99 >99 Me InCl3 (1) 30 1.2 >99 >99 none 30 8 20 >99 Me COOH Cu(NO3)2 (10) 30 12 >99 >99 O Et AlCl3 (1) 30 0.75 >99 >99 InCl3 (1) 30 8 >99 >99 COOH none 30 1.5 12 >99 O Cu(NO3)2 (10) 30 0.25 >99 >99 Ph InCl3 (10) 30 0.02 >99 >99 Me COOH none 65 20 >99 >99 O AlCl3 (1) 65 0.25 99 99 Ph InCl3 (1) 65 2 >99 >99 none 30 0.25 2 99 COOH Cu(NO3)2 (10) 30 0.25 >99 >99 O AlCl3 (1) 30 0.25 98 >99 InCl3 (1) 30 1.5 >99 >99 a. Reaction conversion. ISSN 1424-6376 Page 305 ©ARKAT USA, Inc