Kinetic evidence for a methanolysis intermediate in aromatic nucleophilic substitution

The reactions of 2,4- and 2,6-dinitrochlorobenzene and 2,4-dinitroanisole with cyclohexylamine in benzene and in methanol have been examined. Computer analysis of the kinetic data shows the formation and fate of a solvolysis product in the reaction of 2,4-dinitrochlorobenzene in methanol. The result...

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Autor principal: Nudelman, N.S
Otros Autores: Garrido, D.
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: 1976
Acceso en línea:Registro en Scopus
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100 1 |a Nudelman, N.S. 
245 1 0 |a Kinetic evidence for a methanolysis intermediate in aromatic nucleophilic substitution 
260 |c 1976 
270 1 0 |m Nudelman, N.S.; Dep. de Química Orgánica, Facultad de Cs. Exactas y Naturales, Ciudad Universitaria, Buenos Aires, Argentina 
506 |2 openaire  |e Política editorial 
504 |a Bunnett, J.F., Zahler, R.E., (1951) Chem. Rev, 49, p. 271 
504 |a Brady, O.L., Cropper, F.R., (1950) J. Chem. Soc, p. 507 
504 |a Cavell, E.A.S., Chapman, N.B., (1953) J. Chem. Soc, p. 3392 
504 |a Chapman, N.B., Parker, R.E., Soanes, P.W., (1954) J. Chem. Soc, p. 2109 
504 |a Catclipole, A.G., Lynch, R.H., (1966) Chem. and Ind, 49, p. 2058 
504 |a Suhr, H., (1966) Tetrahedron Letters, 47, p. 5871 
504 |a Brewis, D.M., Chapman, N.B., Paine, J.S., Shorter, J., Wright, D.J., (1974) J.C.S. Perkin II, p. 1787 
504 |a Timmermans, J., Roland, H., (1959) J. chim. Phys, 56, p. 984 
504 |a Nudelman, N.S., Brieux, J.A., (1970) Anales A soc. quim. Argentina, 58, p. 207 
504 |a Crocker, H.P., Hall, R.H., (1955) J. Chem. Soc, p. 4489 
504 |a Bunnett, J.F., Garst, R.H., (1968) J. Org. Chem, 33, p. 2320 
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504 |a Bunnett, J.F., Moe, H., Knutson, D., (1954) J. Amer. Chem. Soc, 76, p. 3936 
504 |a Kost, A.N., Terent’ev, A.P., Shvekhgeimer, G.A., (1951) Izvest. Akad. Nauk S.S.S.R., Otdel. Khim. Nauk, p. 150 
504 |a Kost, A.N., Terent’ev, A.P., Shvekhgeimer, G.A., (1951) Chem. Abs, 45. , 10195c 
504 |a Vogel, A.I., (1956) Practical Organic Chemistry, 168p. , Longman, London, 3rd edn 
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504 |a Bunnett, J.F., Kato, T., Nudelman, N.S., Fundamental Organic Chemistry Laboratory Manual, 112p. , K. Thomas Finley and J. Wilson, Prentice Hall, New Jersey 
504 |a Bernasconi, C.F., (1973) M.T.P. International Rev. Sci. Org. Chem. Ser. 1, 3, p. 33 
504 |a Bunnett, J.F., Bernasconi, C.F., (1970) J. Org. Chem, 35, p. 70 
504 |a N. S. Nudelman and J. A. Brieux, unpublished results; Bunnett, J.F., Morath, R.J., (1955) J. Amer. Chem. Soc, 77, p. 5051 
504 |a Ross, S.D., Finkelstein, M., (1963) J. Amer. Chem. Soc, 85, p. 2603 
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504 |a Beckwith, A.L., Miller, J., Leahy, G.D., (1952) J. Chem. Soc, p. 3552 
504 |a Bunnett, J.F., Nudelman, N.S., (1969) J. Org. Chem, 34, p. 2043 
504 |a Gurney, R.W., (1953) Ionic Processes in Solution, p. 122. , Dover, New York 
504 |a Bunnett, J.F., (1974) Techniques of Chemistry, 6, 406p. , E. S. Lewis, Wiley, New York, ch. VIII 
504 |a Bunnett, J.F., Kato, T., Nudelman, N.S., (1969) J. Org. Chem, 34, p. 785 
520 3 |a The reactions of 2,4- and 2,6-dinitrochlorobenzene and 2,4-dinitroanisole with cyclohexylamine in benzene and in methanol have been examined. Computer analysis of the kinetic data shows the formation and fate of a solvolysis product in the reaction of 2,4-dinitrochlorobenzene in methanol. The results prove that an experimental failure to detect a solvolysis product is not evidence for a negligible solvolysis rate.  |l eng 
593 |a Dep. de Química Orgánica, Facultad de Cs. Exactas y Naturales, Ciudad Universitaria, Buenos Aires, Argentina 
700 1 |a Garrido, D. 
773 0 |d 1976  |h pp. 1256-1260  |k n. 11  |x 1472779X  |t Journal of the Chemical Society, Perkin Transactions 2 
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