Cyanomethyl Esters: Useful Protection for Carboxylic Acids

References

• Mander , L. N. 1988 . Nat. Product Reports , 5 : 541
   Web of Science ®Google Scholar
• Kirkwood , P. S. and MacMillan , J. 1980 . Chem. Soc. Perkin Trans I , : 2117
   Google Scholar
• Nagata , W. , Wakabayashi , T. , Narisada , M. , Hayase , Y. and Kumata , S. 1971 . J. Am. Chem. Soc. , 103 : 5740
   Google Scholar
• Bartlett , P. A. and Johnson , W. S. 1970 . Tetrahedron Lett. , : 4459
   Web of Science ®Google Scholar
• Yamaguchi , I. , Takahashi , N. and Fujita , K. J. 1975 . Chem. Soc., Perkin Trans. 1 , : 992
   Google Scholar
• Hydrogenolysis is obviously not feasible, while the double bond readily migrates into the endocyclic position in anhydrous acidic media or is hydrated in aqueous acid
   Google Scholar
• Green , T. W. 1981 . Protective Groups in Organic Synthesis , New York : John Wiley & Sons, Inc. .
   Google Scholar
• Haslam , E. 1973 . Protective Groups in Organic Chemistry , Edited by: McOmie , J. F.W. London : Plenum press .
   Google Scholar
• Serebryakov , E. P. 1977 . Z. Chem. , 17 : 372
   Google Scholar
• Stewart , F. H.C. 1970 . Aust. J. Chem. , 23 : 2147
   Google Scholar
• A further method for hydrolysis is to heat the cyanomethyl esters with N-bromosuccinimide (1.2 equiv.) in CCl4-CH2Cl4 at reflux for 2 hours, followed by warming with H2O. This method is not compatible with the gibberellin molecule, however
   Google Scholar