References
- Supported by the National Science Foundation (Grant No. CHE-77–28366)
- Gassman , P. G. and Schenk , W. N. 1977 . J. Org. Chem. , 42 : 918 P. G. Gassman, P. K. G. Hodgson, R. J. Balchunis, J. Am. Chem. Soc., 98, 1275. (1976)
- Regen , S. L. , Quici , S. and Liaw , S. 1979 . J. Org. Chem. , 44 : 2029 S. L. Regen, M. D. Ryan, S. Quici, J. Am. Chem. Soc., 101, 7629. (1979); S. L. Regen, S. Quici, J. Org. Chem. 45, 1700. (1980); S. L. Regen, S. Quici, J. Org. Chem., 44, 3436. (1979)
- In contrast to “anydrous hydroxide”, reagent 1 proved ineffective for amide hydrolysis. Thus, less than 10% hydrolysis was observed for N, N-diethylbenzamide, acetamide and acetanilide (procedures used were similar to those used for ester hydrolysis; the reaction time and solvent were 24. h and toluene respectively.)
- Castells , J. J. and Fletcher , G. A. 1956 . J. Chem. Soc. , : 3245 M. Fieser, L. Fieser, “Reagents for Organic Synthesis”, vol. 2, p. 18, Wiley-Interscience, New York
- Brimeyer , M. O. , Mehrotra , A. , Quici , S. , Nigam , A. and Regen , S. L. 1980 . J. Org. Chem. , 45 : 4254 Three types of basic alumina were prepared and compared with 1 for hydrolysis of methyl benzoate: 2 (Castell's reagent, 1.0. g of KOH dissolved in 0.75. mL of water was added to 10. g of neutral alumina); 3 (2.0. g of KOH dissolved in 1.5. mL of water was added to 2.0. g of neutral alumina and was dried [24. h, 60°C (0.1. mm)]); 4 (same as 3. except the drying temperature was 110°C). Hydrolysis of 1.2. g of methyl benzoate in 25. mL of toluene for 2. h using 1, 2, 3, and 4 at room temperature afforded 85, 40, 54. and 0% yields, respectively, of benzoic acid. Control experiments carried out with crushed KOH or with crushed alumina (dried at 100°C for 24. h (0.1. mm)) showed no evidence of hydrolysis. These data imply that a small but finite quantity of water is required for high hydrolytic activity. Similar observations have been made for a KSCN/Silica reagent used to convert epoxides into episulfides