Reaction pathways for ambident aryloxide O- and C-nucleophiles in SNAr displacement versus Meisenheimer complex formation with picryl halides. Stereoelectronic effects on regioselectivity

Journal of Physical Organic Chemistry

Volumn 9, Issue 8, 1996, Pages 515-528

  Manderville, Richard A ^a   Dust, Julian M ^b   Buncel, Erwin ^c  

^a WAKE FOREST UNIVERSITY   (United States)

^b MEMORIAL UNIVERSITY OF NEWFOUNDLAND   (Canada)

^c QUEEN S UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0008124655     PISSN: 08943230     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-1395(199608)9:8<515::AID-POC816>3.0.CO;2-5     Document Type: Article

References (8)

1. E. Buncel, R. A. Manderville and J. M. Dust, Zh. Org. Khim. Submitted.
2. E. Buncel, M. R. Crampton, M. J. Strauss and F. Terrier, Electron Deficient Aromatic- and Heteroaromatic-base Interactions. The Chemistry of Anionic Sigma Complexes. Elsevier, Amsterdam (1984).
3. E. Buncel, in The Chemistry of Functional Groups. Supplement F. The Chemistry of Amino Nitro and Nitroso Compounds, pp. 1225-1260, edited by S. Patai, Wiley, Chichester (1982);
4. (a) G. A. Artamkina, M. P. Egorov and I.P. Beletskaya, Chem. Rev. 82, 427 (1982).
5. (b) F. Terrier, Chem. Rev. 82, 77 (1982).
6. J. Meisenheimer, Justus Liebigs Ann. Chem. 323, 205 (1902).
7. (a) C. J. Jackson and W. F. Boos. Am. Chem. J. 20, 444 (1898);
8. (b) C. J. Jackson and P. H. Gazzolo, J. Am. Chem. Soc. 23, 376 (1900)