Evaluation of Electrophilic Activities of Substituted Nitroarenes in the VNS Reaction with Secondary and Tertiary Carbanions

• Autorzy: Błażej S. , Wileńska B. , Voynova N. S. , Mąkosza M.
• Języki publikacji: EN

Abstrakty

EN

Relative electrophilic activities of substituted nitroarenes in the vicarious nucleophilic substitution (VNS) reaction with carbanion of chloromethyl p-chlorophenyl and bromo - methyl phenyl sulfones, 1 and 2, were determined via competitive experiments. The results are in good agreement with relative activities determined earlier in the competitive experiments with carbanion of chloromethyl phenyl sulfone 3 confirming reliability of these data. On the other hand, analogous competitive experiments with tertiary carbanions of chloroform and 1-chloroethyl phenyl sulfone gave results much affected by steric effects thus the VNS reaction with these carbanions can not be used for evaluation of electrophilic activities of nitroarenes.

Słowa kluczowe

EN

vicarious nucleophilic substitution (VNS); carbanions; competitive experiments; nitroarenes; electrophilic activity

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2008
• Tom: Vol. 82, nr 10
• Strony: 2017--2030
• Opis fizyczny: Bibliogr. 19 poz., rys.

Twórcy

autor

Błażej S.

autor

Wileńska B.

autor

Voynova N. S.

autor

Mąkosza M.

• Institute of Organic Chemistry Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland Fax: [phone],

Bibliografia

• 1.   Błażej S. and Mąkosza M., Chem. Ew. J. (submitted).
• 2.   Seeliger F., Błażej S., Bernhardt S., Mąkosza M. and Mayr H., Chem. Eur. J. (in print).
• 3.   Miller J., Aromatic Nucleophilic Substitution, Elsevier: Amsterdam 1968.
• 4.   Terrier R, Nucleophilic Aromatic Displacement: The Influence of the Nitro Group, Organic Nitro Chemistry series, VCH: New York 1991.
• 5.   Bunnet J.R and Zahler R.E., Chem. Rev., 49, 273 (1951).
• 6.   Chupakhin O.N., Charushin V.N. and Van der Plas H.C., Nucleophilic Aromatic Substitution of Hydrogen, Academic Press: San Diego 1994.
• 7.   Mąkosza M., Russ. Chem. Bull., 45,491 (1996).
• 8.   Mąkosza M. and Wojciechowski K., Chem. Rev., 104, 2631 (2004).
• 9.   Goliński J. and Mąkosza M., Tetrahedron Lett., 37, 3495 (1978).
• 10.   Mąkosza M. and Winiarski J., Acc. Chem. Res., 20, 282 (1987).
• 11.   Mąkosza M. and Wojciechowski K., Liebigs Ann. J. Recueil, 9, 1805 (1997).
• 12.   Mąkosza M. and Sienkiewicz K., J. Org. Chem., 63, 4199 (1998).
• 13.   Lemek T., Mąkosza M., Stephenson D.S. and Mayr H., Angew. Chem. Int. Ed., 42, 2793 (2003).
• 14.   Mąkosza M. and Kwast A., J. Phys. Org. Chem., 11, 341 (1998).
• 15.   Mąkosza M., Lemek T., Kwast A. and Terrier R, J. Org. Chem., 67, 394 (2002).
• 16.   Mąkosza M. and Owczarczyk Z., J. Org. Chem., 54, 5094 (1989).
• 17.   Vogel A.I., Textbook of Practical Organic Chemistry, 5th Ed., Prentice Hali, 1989.
• 18.   Mąkosza M. and Goliński J., J. Org. Chem. 49,1488 (1984).
• 19.   Mąkosza M., Glinka T. and Kinowski A. Tetrahedron, 40, 1863 (1984).