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Original Articles

ACYLATION AND ALKYLATION OF 2- AND 4-METHYLBENZONITRILE

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Pages 407-412 | Received 06 Jun 1999, Accepted 10 Aug 1999, Published online: 11 Feb 2009

REFERENCES

  • Simchen , G. and Häfner , M. 1974 . Ann. , : 1802 b) L. Arsenijevic and V. Arsenijevic, Bull. Soc. Chem. Fr., 3403 (1968)
  • Beugelmans , R. , Bois-Choussy , M. and Boudet , B. 1982 . Tetrahedron , 38 : 3479 In this reaction, basic workup resulted in a retro-Claisen fragmentation of the initial addition product to give the cyano ester
  • Bradsher , C. K. and Wallis , T. G. 1978 . J. Org. Chem. , 43 : 3817 Acylation of 2-methylbenzonitrile with diethyl carbonate using NaNH2 in NH3 gave ethyl (2-cyanophenyl)acetate in 25% yield, see. An earlier paper also described acylations with carboxylic esters under similar conditions, see W. T. Boyce and R. Levine, ibid., 31, 3807 (1966)
  • Meth-Cohn , O. and Wang , M.-X. 1997 . Chem. Commun. , : 1041 b) O. Meth-Cohn and M.-X. Wang, J, Chem. Soc., Perkin Trans. I, 3197 (1997)
  • Rash , F. H. , Boatman , S. and Hauser , C. R. 1967 . J. Org. Chem. , 32 : 372 Alkylations of 2- and 4-methylbenzonitrile using NaNH2 in NH3 have been reported, see
  • Kaiser , E. M. and Petty , J. D. 1976 . J. Organomet. Chem. , 107 : 219 One other report has described the deprotonation of 2-methylbenzonitriles by LDA for an annulation procedure, see K. Kobayashi, T. Uneda, K. Takada, H. Tanaka, T. Kitamura, O. Morikawa and H. Konishi, J. Org. Chem., 62, 664 (1997)
  • Mukhopadhyay , T. and Seebach , D. 1982 . Helv, Chim. Acta , 65 : 385 The use of DMPU in the current reaction gave cleaner conversion to the products
  • Rathke , M. W. and Deitch , J. 1971 . Tetrahedron Lett. , : 2953
  • Nahm , S. and Weinreb , S. M. 1981 . Tetrahedron Lett. , 22 : 3815 For a large-scale synthesis of N, O-dimethylhydroxylamine hydrochloride, see O. P. Goel and U. Krolls, Org. Prep. Proced. Int., 19, 75 (1987)
  • Still , W. C. , Kahn , M. and Mitra , A. 1978 . J. Org. Chem. , 43 : 2923

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