26. SNAr reactions of amines in aprotic solvents |
1295 |
throughout almost two decades devoted to the study of SNAr reactions are heartily acknowledged.
VI. REFERENCES
1.For recent reviews see:
(a)F. Terrier, ‘Nucleophilic aromatic displacement: The influence of the nitro group’, in Organic Nitro Chemistry Series (Ed. H. Ferrer), VCH Publishers, New York, 1991.
(b)N. S. Nudelman, An. Acad. Nac. Ciencias Exactas (Buenos Aires), 32, 109, (1980).
(c)C. F. Bernasconi, MTP Int. Rev. Sci., Org. Chem. Ser. 1, 3, 33, (1973).
(d)J. F. Bunnett and J. J. Randall, J. Am. Chem. Soc., 80, 6020 (1958).
2.(a) J. F. Bunnett and R. J. Garst, J. Am. Chem. Soc., 87, 3875 (1965).
(b)J. F. Bunnett and R. J. Garst, J. Am. Chem. Soc., 87, 3879 (1965).
(c)J. F. Bunnett and R. J. Morath, J. Am. Chem. Soc., 77, 5051 (1955).
3.(a) C. F. Bernasconi, Acc. Chem. Res., 11, 147 (1978).
(b)C. F. Bernasconi, Chimia, 324, 1 (1980).
4.(a) N. S. Nudelman and J. A. Brieux An. Asoc. Quim. Arg., 207 (1978).
(b)N. S. Nudelman and J. A. Brieux, An. Asoc. Quim. Arg., 217 (1978).
5.F. Terrier, Chem. Rev., 82, 77 (1982).
6.(a) R. Bacaloglu, A. Blasko, C. A. Bunton, E. Dorwin, F. Ortega and C. Zucco, J. Am. Chem. Soc., 113, 238 (1991) and references cited therein.
(b)R. Bacaloglu, C. A. Bunton and F. Ortega, J. Am. Chem. Soc., 111, 1041 (1989).
(c)R. Bacaloglu, C. A. Bunton and F. Ortega, J. Am. Chem. Soc., 110, 3503 (1988).
7.J. I. Hayami, S. Otani, F. Yamaguchi and Y. Nishikawa, Chem. Lett., 739 (1987).
8.L. Forlani, M. Sintoni and P. E. Todesco, J. Chem. Res. (S), 66, 344 (1986).
9.S. M. Chiacchiera, J. O. Singh, J. D. Anunziata and J. J. Silber, J. Chem. Soc., Perkin Trans. 2, 1585 (1988).
10.N. S. Nudelman, J. Phys. Org. Chem., 2, 1 (1989) and references cited therein.
11. (a) E. Buncel, M. R. Crampton, M. J. Strauss and F. Terrier. In Electron-Deficient Aromatic and Heteroaromatic Base Interactions, Elsevier, Amsterdam, 1984.
(b)G. A. Artamkina, M. P. Egorov and I. P. Beletskaya, Chem. Rev., 82, 427 (1982).
12.N. S. Nudelman and S. B. Cerdeira, Magn. Reson. Chem., 24, 1098 (1986).
13.(a) D. A. De Bie, B. Geurtsen, I. E. Berg and H. C. Van der Plas, J. Org. Chem., 51, 3209 (1986).
(b)H. C. Van der Plas, M. Wozniak and H. J. Van der Haak, Adv. Heterocycl. Chem., 33, 96 (1983).
14.K. Bowden, S. Prasannan and R. J. Ranson, J. Chem. Soc., Perkin Trans. 2, 181 (1987).
15.(a) F. Bazzani, P. Mencarelli and F. Stegel, J. Org. Chem., 49, 2375 (1984).
(b)A. Annulli, P. Mencarelli and F. Stegel, J. Org. Chem., 49, 4065 (1984).
16.J. D. Reinheimer, N. Sourbais, R. L. Lavallee and D. Goodwin and G. L. Gould, Can. J. Chem., 62, 1120 (1984).
17.F. Terrier, A. P. Chatrouse, P. Soudais and M. Hlaibi, J. Org. Chem., 49, 4176 (1984).
18.C. F. Bernasconi and R. H. de Rossi, J. Org. Chem., 41, 44 (1976).
19.J. A. Orvick and J. F. Bunnett, J. Am. Chem. Soc., 92, 2417 (1970).
20.(a) J. F. Bunnett and A. V. Cartano,˜ J. Am. Chem. Soc., 103, 4861 (1981).
(b)J. F. Bunnett, S. Sekiguchi and L. A. Smith, J. Am. Chem. Soc., 103, 4865 (1981).
(c)S. Sekiguchi and J. F. Bunnett, J. Am. Chem. Soc., 103, 4871 (1981).
21.(a) S. Sekiguchi, M. Hosokawa, T. Suzuki and M. Sato, J. Chem. Soc., Perkin Trans. 2, 1111 (1993).
(b)H. Fujinuma, M. Hosokawa, T. Suzuki, M. Sato and S. Sekiguchi, Bull. Chem. Soc. Jpn., 62, 1969 (1989).
22.(a) Y. Hasegawa, Bull. Chem. Soc. Jpn., 56, 1314 (1983).
(b)Y. Hasegawa, J. Org. Chem., 50, 649 (1985).
23.Y. Hasegawa, J. Chem. Soc., Perkin Trans. 2, 547 (1984).
24.M. R. Crampton and P. J. Routledge, J. Chem. Soc., Perkin Trans. 2, 573 (1984).
25.R. H. de Rossi and R. A. Rossi, J. Org. Chem., 39, 3486 (1974).
26.T. O. Bamkole, J. Hirst and G. Hussain, J. Chem. Soc., Perkin Trans. 2, 681 (1984).
27.E. R. de Vargas and R. H. de Rossi, J. Org. Chem., 49, 3978 (1984).
28.F. Del Cima, G. Biggi and F. Pietra, J. Chem. Soc., Perkin Trans. 2, 559 (1983).
1296 |
Norma S. Nudelman |
29.(a) C. Paradisi and G. Scorrano, in Nucleophilicity (Eds. J. M. Harris and S. P. Mc Manus), ACS Advances in Chemistry Series, No 215, American Chemical Society: Washington, DC, 1987, p. 339.
(b)V. Arca, C. Paradisi and G. Scorrano, J. Org. Chem., 55, 3617 (1990).
(c)C. Paradisi, U. Quintilli and G. Scorrano, J. Org. Chem., 48, 3022 (1983).
30.(a) C. A. Bunton, J. R. Moffatt and J. Spillane, J. Chem. Soc., Perkin Trans. 2, 1799 (1986).
(b)V. Athanassakis, C. A. Bunton and F. de Buzzaccarini, J. Phys. Chem., 86, 5002 (1982).
31.(a) T. J. Broxton, J. R. Christie and A. J. Dole, J. Phys. Org. Chem., 7, 442 (1994).
(b)T. J. Broxton, J. R. Christie and D. Theodoridis, J. Phys. Org. Chem., 6, 535 (1993).
32.(a) A. Cipciani, R. Germani, G. Savelli, C. A. Bunton, M. Mhala and J. R. Moffatt, J. Chem. Soc., Perkin Trans. 2, 541 (1987).
(b)A. Cipciani, M. C. Fracasini, R. Germani, G. Savelli and C. A. Bunton, J. Chem. Soc., Perkin Trans. 2, 547 (1987).
33.E. N. Durantini, S. M. Chiacchiera and J. J. Silber, J. Org. Chem., 58, 7115 (1993).
34.M. Gisler and H. Zollinger, Angew. Chem., Int. Ed. Engl., 20, 203 (1981).
35.F. Schmidtchen, Chem. Ber., 117, 725, 1287 (1984).
36.S. E. Fry and N. J. Pienta, J. Am. Chem. Soc., 107, 6399 (1985).
37.C. F. Reichardt, Solvents and Solvent Effects in Organic Chemistry, 2nd ed., VCH, Weinheim, 1988.
38.(a) M. J. Kamlet, J. L. Abboud, M. Abraham and R. W. Taft, J. Org. Chem., 48, 2877 (1983).
(b)J. L. Abboud, M. J. Kamlet and R. W. Taft, Prog. Phys. Org. Chem., 13, 485 (1981).
39.M. J. Kamlet and R. W. Taft, Acta Chem. Scand. Ser B, 39, 611 (1985).
40.M. H. Abraham, J. Phys. Org. Chem., 1994, 7, 655 (1994).
41.(a) M. J. Kamlet, J. -L. M. Abboud, M. H. Abraham and R. W. Taft, J. Org. Chem., 48, 2877 (1983).
(b)R. W. Taft, J. -L. M. Abboud, M. J. Kamlet and M. H. Abraham, J. Solution Chem., 14, 153 (1983).
42.M. H. Abraham, P. L. Grelier, J. -L. M. Abboud, R. M. Doherty and R. W. Taft, Can. J. Chem., 66, 153 (1988).
43.S. Supan J. Photochem. Photobiol., A50, 293 (1990).
44.R. Nakagaki, I. Aoyama, K. Shimizu and M. Akagi J. Phys. Org. Chem., 6, 261 (1993).
45.(a) Y. Migron and Y. Marcus, J. Phys. Org. Chem., 4, 310 (1991).
(b)Y. Migron and Y. Marcus, J. Phys. Chem., 95, 400 (1991).
46.T. W. Bentley, Am. Chem. Soc. Ser., 215, 255 (1987).
47.D. N. Kevill and S. W. Anderson, J. Am. Chem. Soc., 108, 1579 (1986).
48.(a) P. M. E. Mancini, R. D. Martinez, L. R. Vottero and N. S. Nudelman, J. Chem. Soc., Perkin Trans. 2, 1133 (1984).
(b)R. D. Martinez, P. M. E. Mancini, L. R. Vottero and N. S. Nudelman, J. Chem. Soc., Perkin Trans. 2, 1427 (1986).
(c)N. S. Nudelman, R. D. Martinez, P. M. E. Mancini and L. R. Vottero, An. Soc. Cient. Arg., 211, 27 (1981).
49.(a) J. Lelievre, O. Haddad-Fahed and R. Gaboriaud, J. Phys. Chem., 84, 449 (1987).
(b)J. Lelievre, O. Haddad-Fahed and R. Gaboriaud, J. Chem. Soc., Faraday Trans. 1, 82, 2301 (1986).
50.M. H. Abraham, P. L. Grelier, D. V. Prior, J. J. Morris and P. J. Taylor, J. Chem. Soc., Perkin Trans. 2, 521 (1990).
51.M. H. Abraham, P. L. Grelier, D. V. Prior, R. W. Taft, J. J. Morris, P. J. Taylor, C. Laurence, M. Berthelot, R. M. Doherty, M. J. Kamlet, J. -L. M. Abboud, K. Sraidi and G. Guiheneuf, J. Am. Chem. Soc., 110, 8534 (1988).
52.M. H. Abraham and M. Roses, J. Phys. Org. Chem., 7, 672 (1994).
53.K. G. Millar and C. F. Poole, J. High Resolut. Chromatogr., 17, 125 (1994).
54.M. H. Abraham, J. Phys. Org. Chem., 6, 660 (1993).
55.M. H. Abraham, Pure Appl. Chem., 65, 2503 (1993).
56.M. H. Abraham, H. S. Chadha, G. S. Whiting and R. C. Mitchell, J. Pharm. Sci., 83, 1085 (1994).
57.D. E. Leahy, J. J. Morris, P. J. Taylor and A. R. Wait, J. Chem. Phys., 89, 1597 (1992).
58.D. E. Leahy, J. J. Morris, P. J. Taylor and A. R. Wait, J. Chem. Soc., Perkin Trans. 2, (a) 705,
(b)723 (1992).
26. SNAr reactions of amines in aprotic solvents |
1297 |
59.M. H. Abraham, H. S. Chadha and R. C. Mitchell, J. Pharm. Sci., 83, 1257 (1994).
60.D. E. Leahy, J. J. Morris, P. J. Taylor and A. R. Wait, J. Phys. Org. Chem., 7, 743 (1994).
61.Y. Marcus, Ion Solvation, Wiley, New York, 1995.
62.E. Bosch, F. Rived and M. Roses, J. Phys. Org. Chem., 7, 696 (1994).
63.Y. Marcus, J. Solution Chem., 20, 929 (1991).
64.Y. Migron and Y. Marcus, J. Chem. Soc., Faraday Trans., 87, 1339 (1991).
65.E. Bosch, C. Rafols and M. Roses, Anal. Chem., 62, 102 (1990).
66.M. Roses, F. Rived and E. Bosch, J. Chem. Soc., Faraday Trans., 89, 1723 (1993).
67.E. Casassas, G. Fonrodona, A. de Juan and R. Tauler, Chemometr. Intell. Lab. Syst., 12, 29 (1991).
68.M. H. Abraham, Chem. Soc. Rev., 22, 73 (1993).
69.M. H. Abraham, Pure Appl. Chem., 65, 2503 (1993).
70.M. H. Abraham, J. Phys. Org. Chem., 6, 660 (1993).
71.M. H. Abraham, H. S. Chadha, G. S. Whiting and R. C. Mitchell, J. Pharm. Sci., 83, 1085 (1994).
72.M. H. Abraham and M. Roses, J. Phys. Org. Chem., 7, 672 (1994).
73.M. H. Abraham, H. S. Chadha and R. C. Mitchell, J. Pharm. Sci., 83, 1257 (1994).
74.M. H. Abraham, H. S. Chadha, J. P. Dixon and A. J. Leo, J. Phys. Org. Chem., 7, 712 (1994).
75. R. M. C. Goncalves, A. M. N. Simoes, L. M. P. C. Albuquerque, M. Roses, C. Rafols and
E. Bosch, J. Chem. Res., (M) 1380; (S) 214 (1993).
76.F. G. Bordwell and D. L. Hughes, J. Am. Chem. Soc., 108, 5991 (1986).
77.J. R. Gandler, I. U. Setiarahardjo, C. Tufon and C. Chen, J. Org. Chem., 57, 4169 (1992).
78.A. V. Veglia and R. H. de Rossi, Indian J. Technol., 30, 397 (1992).
79.E. B. de Vargas, M. V. Remedi and R. H. de Rossi, J. Phys. Org. Chem., 8, 113 (1995).
80.(a) C. D. Ritchie, Acc. Chem. Res., 5, 348 (1972).
(b) C. D. Ritchie and P. O. I. Virtanen, J. Am. Chem. Soc., 95, 1882 (1973).
(c) C. D. Ritchie and M. Sawada, J. Am. Chem. Soc. 99, 3754 (1977).
81.J. F. Bunnett and N. S. Nudelman J. Org. Chem., 34, 2038 (1969) and references cited therein.
82.N. S. Nudelman and S. Cerdeira, J. Chem. Soc., Perkin Trans. 2, 695 (1986).
83.(a) N. S. Nudelman and P. Mac Cormack, J. Chem. Soc., Perkin Trans. 2, 227 (1987).
(b) N. S. Nudelman and P. Mac Cormack, Tetrahedron, 40, 4227 (1984).
84.E. D. Raczynska, P. C. Maria and M. Decouzon, in Proceedings of the 12th International Mass Spectrometry Conference, 1991.
85.M. Decouzon, J. F. Gal, P. C. Maria and E. D. Raczynska, Rapid Commun. Mass Spectrom., 7, 599 (1993).
86.E. D. Raczynska, P. C. Maria, J. F. Gal and M. Decouzon, J. Phys. Org. Chem., 7, 725 (1994).
87.(a) I. A. Koppel, F. Anvia and R. W. Taft, J. Phys. Org. Chem., 7, 717 (1994).
(b) M. Berthelot, M. Helbert, C. Laurence, J. -Y. LeQuestel, F. Anvia and R. W. Taft, J. Chem. Soc., Perkin Trans. 2, 625 (1993).
88.R. W. Taft and R. D. Topsom, Prog. Phys. Org. Chem., 16, 1 (1987).
89.I. A. Koppel, U. H. Molder and R. J. Pikver, in Electron and Proton Affinities of Molecules, 1991, pp. 5 112. USSR Academy of Sciences Press, Ufa
90.M. Meot-Ner (Mautner) and L. W. Sieck, J. Am. Chem. Soc., 113, 4448 (1991).
91.J. E. Szuleijko and T. B. McMahon, J. Mass, Spectrom, Ion Processes, 109, 279 (1991).
92.J. E. Szuleijko and T. B. McMahon, J. Am. Chem. Soc., 115, 7839 (1993).
93. I. A. Koppel, R. W. Taft, F. Anvia, S..Z. Zhu, L. Q. Hu, K. S. Sung, D. D. DesMarteau, L. M. Yagupolskii, Yu. L. Yagupolskii, N. V. Ignat’ev, N. V. Kondratenko, A. Y. Volkonskii,
V. M. Vlasov, R. Notario and P. C. Maria, J. Am. Chem. Soc., 116, 3047 (1994).
94.R. W. Taft and R. D. Topsom, Prog. Phys. Org. Chem., 16, 1 (1987).
95.C. Hansh, A. Leo and R. W. Taft, Chem. Rev., 91, 165 (1991).
96.S. Gupta, Chem. Rev., 87, 1183 (1987).
97.A. D. Headley, S. D. Strarness, E. T. Cheung and P. L. Malone, J. Phys. Org. Chem., 8, 26 (1995).
98.R. W. Taft, Prog. Phys. Org. Chem., 16, 120 (1987).
99.A. D. Headley and M. E. McMurray, J. Phys. Org. Chem., 7, 63 (1994).
100.A. D. Headley, J. Phys. Org. Chem., 4, 3688 (1991).
101.V. O. Chechik and V. A. Bobylev, Zh. Onshch, Khim., 1993, 63, 1502
102.N. S. Nudelman J. Org. Chem., 30, 3356 (1965).
1298 |
Norma S. Nudelman |
103.(a). G. Consiglio, R. Notto and D. Spinelli J. Chem. Soc., Perkin Trans. 2, 222 (1979).
(b)D. M. Brewis, N. B. Chapman, J. S. Paine, J. Shorter and D. J. Wright, J. Chem. Soc. Perkin Trans. 2, 1787 (1974).
(c)G. Becker, C. F. Bernasconi and H. Zollinger, Helv. Chim. Acta, 49, 10 (1966).
104.(a) N. S. Nudelman and D. Palleros, J. Chem. Soc., Perkin Trans 2, 805 (1985).
(b)D. Palleros and N. S. Nudelman An. Soc. Cient. Arg., 43, 3 (1986).
105.(a) S. C. Nyburg, C. H. Faerman, L. Prasad, D. Palleros and N. S. Nudelman Acta Crystallogr., C43, 686 (1987).
(b)N. S. Nudelman and D. Garrido, J. Chem. Soc., Perkin Trans. 2, 1256 (1976).
106.(a) C. Hansch, A. Leo and R. W. Taft, Chem. Rev., 91, 165 (1991).
(b)R. W. Taft, J. Chim. Phys., 89, 1557 (1992).
107.N. S. Nudelman and D. Palleros J. Chem. Soc., Perkin Trans. 2, 995 (1981).
108.C. F. Bernasconi, J. Phys. Chem. 75, 3636 (1971).
109.T. A. Emokpae, P. U. Uwakwe and J. Hirst, J. Chem. Soc., Perkin Trans. 2, 509 (1991).
110.S. M. Chiacchiera, R. I. Cattana, J. O. Singh, J. D. Anunziata and J. J. Silber, J. Phys. Org. Chem., 2, 631 (1989).
111.F. Pietra and D. Vitali, J. Chem. Soc., Perkin Trans. 2, 385 (1972).
112.G. A. Jeffrey and W. Saenger, Hydrogen Bonding in Biological Molecules, Springer-Verlag, Berlin Heidelberg, 1991.
113.K. Tamaru and M. Ichikama, Catalysis by Electron-Donor-Acceptor Complexes, Wiley, New York, 1975.
114.(a) O. B. Nagy, Bull. Soc. Chim. Belg., 94, 11 (1985).
(b)O. B. Nagy, M. Wa Muanda and J. B. Nagy, J. Chem. Phys., 83, 1961 (1979).
115.(a) E. Durantini, L. Zingaretti, J. D. Anunziata, and J. J. Silber, J. Phys. Org. Chem., 5, 557 (1992).
(b)L. Giacomelli, R. Cattana, J. D. Anunziata, J. J. Silber, M. Hedrera, S. Salerno and I. Perillo,
J. Phys. Org. Chem., 7, 162 (1994).
116.(a) J. O. Singh, J. D. Anunziata and J. J. Silber, Can J. Chem., 63, 903 (1985).
(b)S. M. Chiacchiera, J. O. Singh, J. D. Anunziata and J. J. Silber, J. Chem. Soc., Perkin Trans. 2, 987 (1987).
117.R. I. Cattana, J. O. Singh, J. D. Anunziata and J. J. Silber, J. Chem. Soc., Perkin Trans. 2, 79 (1987).
118.(a) S. S. Shaik Pure Appl. Chem., 63, 195 (1991).
(b)S. S. Shaik J. Org. Chem., 52, 1563 (1987).
119.A. Pross, Acc. Chem. Res., 18, 212 (1985).
120. (a) S. S. Shaik, in New Theoretical Concepts for Understanding Organic Reactions (Eds. J. Bertran and J. G. Csizmadia), ed. p. 165. Kluwer, Dordrecht, 1989.
(b)S. S. Shaik J. Am. Chem. Soc., 106, 1227 (1984).
121.D. Bethell and V. D. Parker, J. Phys. Org. Chem., 5, 317 (1992).
122.E. Sinsheimer and A. M. Keuhnelian, Anal. Chem., 44, 89 (1974).
123.L. Forlani, G. Guastadisegni and L. Raffellini, J. Chem. Res. (S), 392 (1989).
124.M. H. Krackov, C. M. Lee and H. G. Mautner, J. Am. Chem. Soc., 99, 4090 (1977).
125.L. Forlani, Gazz. Chim. Ital., 121, 475 (1991).
126.B. Capon and C. W. Rees, An. Rep. Prog. Chem., 60, 279 (1963).
127.J. Hirst, G. Hussain and I. Onyido, J. Chem. Soc., Perkin Trans. 2, 397 (1986).
128.D. Ayediran, T. O. Bamkole and J. Hirst, J. Chem. Soc., Perkin Trans. 2, 1013 (1974).
129.L. Forlani, Gazz. Chim. Ital., 122, 349 (1992).
130.R. Chamberlain and M. R. Crampton, J. Chem. Soc., Perkin Trans. 2, 75 (1993).
131.R. Chamberlain and M. R. Crampton, J. Chem. Soc., Perkin Trans. 2, 425 (1994).
132.M. R. Crampton and J. A. Stevens, J. Chem. Soc., Perkin Trans. 2, 925 (1989).
133.R. Chamberlain and M. R. Crampton, J. Chem. Res. (S), 106; (M), 811 (1993).
134.R. Chamberlain, M. R. Crampton and R. L. Knight, J. Chem. Res. (S), 444; (M), 2986 (1993).
135.T. Ibata and X. Zou, High Pressure Research, 11, 81 (1992).
136.T. Ibata, Y. Isogami and J. Toyoda, Chem. Lett., 1187 (1987); T. Ibata, Y. Isogami and J. Toyoda,
Bull Chem. Soc. Jpn., 64, 42 (1991).
137.K. Matsumoto, T. Uchida, T. Okamoto and S. Hashimoto, Chem. Express. 2, 551 (1987).
138. S. Hashimoto, S. Otani, T. Okamoto and K. Matsumoto, Heterocycles, 27, 319 (1988); K. Matsumoto, T. Uryu and M. Munakata, Chem. Express, 3, 739 (1988).
26. SNAr reactions of amines in aprotic solvents |
1299 |
139.K. Matsumoto, S. Hashimoto, H. Minatogawa, M. Munakata and S. Otani, Chem. Express, 5, 473 (1990).
140.T. Ibata, X. Zou and T. Demura, Tetrahedron Lett., 34, 5613 (1993).
141.T. Ibata, X. Zou and T. Demura, Bull Chem. Soc. Jpn., 67, 196 (1994).
142.T. Ibata, Y. Isogami and J. Toyoda, Chem. Lett., 1187 (1987); Bull Chem. Soc. Jpn., 64, 42 (1991).
´
143. (a) N. S. Nudelman and D. Palleros, Acta Sud. Am. Quim., 1, 125 (1981).
(b) D. Palleros and N. S. Nudelman, Proceedings IInd Phys. Org. Chem. Symposium, Cordoba, 1980; p. 33.
144. N. S. Nudelman and D. Palleros, J. Org. Chem., 48, 1607 (1983).
145. L. Abello, M. Kern, C. Caseres and G. Pannetier, Bull Soc. Chim. France, 94 (1970). 146. J. C. Shug and W. M. Chang J. Phys. Chem., 75, 938 (1971).
147. (a) G. Illuminati, F. La Torre, G. Liggieri, G. Sleiter and F. Stegal J. Am. Chem. Soc., 97, 1851 (1975).
(b) D. M. Brein, J. Chem. Soc., Perkin Trans. 2, 1787 (1974).
(c) G. Becker, C. F. Bernasconi and H. Zollinger, Helv. Chim. Acta, 49, 10 (1966). 148. (a) T. O. Bamkole, J. Hirst and J. Onyido, J. Chem. Soc., Perkin Trans. 2, 889 (1982).
(b) E. T. Akinyele, I. Onyido and J. Hirst, J. Phys. Org. Chem., 3, 41 (1990). 149. (a) L. Forlani and C. Cimarelli, J. Chem. Res. (S), 62 (1982).
(b) L. Forlani and C. Cimarelli, J. Chem. Res. (S), 258 (1982).
(c) L. Forlani, Gazz. Chim. Ital., 112, 205 (1982).
150. O. Banjoko and C. Ezeani, J. Chem. Soc., Perkin Trans. 2, 1357 (1982). 151. G. Guanti, G. Petrillo and S. Thea, Tetrahedron, 38, 505 (1982).
152. V. Frenna, N. Vivona, A. Caronia, G. Consiglio and D. Spinelli., J. Chem. Soc., Perkin Trans. 2, 1203 (1983).
153. J. Hirst, J. Phys. Org. Chem., 7, 68 (1994).
154. O. Banjoko and C. Ezeani, J. Chem. Soc., Perkin Trans 2, 531 (1986).
155. O. Banjoko and I. A. Bayeroju, J. Chem. Soc., Perkin Trans. 2, 1853 (1988). 156. W. P. Jencks, Chem. Soc. Rev., 10, 345 (1981).
157. A. Wolff and G. Gamer, J. Phys. Chem., 76, 871 (1972).
158. J. M. Menger and J. H. Smith, J. Am. Chem. Soc., 91, 4211 (1969).
159. F. Ciuffarin, M. Isola and P. Leoni, J. Org. Chem., 46, 3064 (1981).
160. V. Frena, N. Vivona, G. Consiglio and D. Spinelli, J. Chem. Soc. Perkin Trans. 2, 1865 (1985). 161. A. Reyes and R. M. Scott, J. Phys. Chem., 84, 3600 (1980).
162. J. Hirst, G. N. Onuoha and I. Onyido J. Chem. Soc. Perkin Trans. 2, 971 (1988). 163. (a) C. F. Bernasconi and H. Zollinger, Helv. Chim. Acta, 49, 2570 (1966).
(b) C. F. Bernasconi, M. Kaufmann and H. Zollinger, Helv. Chim. Acta, 49, 2563 (1966). 164. S. D. Ross, Tetrahedron, 25, 4427 (1969).
´
165. R. Cetina, M. Rubio and M. A. Mora Rev. Latinoam. Quim., 10, 50 (1979). 166. (a) P. A. Kollman and L. C. Allen, J. Am. Chem. Soc., 93, 4991 (1971).
(b) J. E. del Bene, J. Am. Chem. Soc., 95, 5460 (1973).
167. a) F. Ratkonis and T. Salamon, Acta Chim. Acad. Sci. Hung., 94, 93 (1977).
(b) M. K. D. Choudhury and H. B. Mathur, Indian J. Chem., A, 14, 735 (1976). 168. J. del Bene, J. Am. Chem. Soc., 102, 5191 (1980).
169. L. Farah, G. Giles, D. Wilson, A. Ohno and R. M. Scott, J. Phys. Chem., 83, 2455 (1979). 170. O. Banjoko and P. Otiono, J. Chem. Soc., Perkin Trans. 2, 399 (1981).
171. J. F. Bunnett and R. H. Garst, J. Org. Chem., 33, 2320 (1968). 172. N. S. Nudelman and D. Palleros, J. Org. Chem., 48, 1612 (1983).
173. A. J. Kresge and M. F. Powell, J. Am. Chem. Soc., 103, 972 (1981).
174. D. Palleros and N. S. Nudelman Acta Sud Am. Quim., 3, 49 (1984).
175. N. S. Nudelman and D. Palleros J. Chem. Soc. Perkin Trans. 2, 1277 (1984).
176. G. Visandul, V. S. Kutz and V. D. Pokhodenko, Zh. Obshch. Khim., 43, 180 (1972).
177. N. S. Nudelman, M. Marder and A. Gurevich, J. Chem. Soc., Perkin Trans. 2, 229 (1993). 178. J. M. Harris, S. P. McManus, M. R. Sedaghat-herati, N. Neamati-Mazraey, R. M. Doherty,
R. W. Taft and M. H. Abraham, Am. Chem. Soc. Ser., 215, 247 (1987).
179.R. W. Taft, T. Gramstad and M. J. Kamlet, J. Org. Chem., 47, 4557 (1982).
180.D. Palleros and N. S. Nudelman, J. Chem. Soc., Perkin Trans. 2, 479 (1985).
181.H. Suhr, Ber. Bunsenges. Phys. Chem., 67, 893 (1963).
1300 |
Norma S. Nudelman |
182.D. Ayediran, T. O. Bamkole, J. Hirst and I. Onyido, J. Chem. Soc., Perkin Trans. 2, 597 (1977).
183.A. V. Ryzhakov, V. V. Vapirov and L. L. Rodina, J. Org. Chem. USSR. (Engl. Transl.), 27, 825 (1991).
184.(a) L. Forlani and C. Cimarelli, J. Phys. Org. Chem., 2, 653 (1989).
(b)L. Forlani, G. Guastadisegni and L. Raffellini, J. Chem. Res. (S), 392 (1989).
185.L. Forlani, J. Chem. Res. (S), 260 (1984).
186.L. Forlani and M. Sintoni, J. Chem. Soc., Perkin Trans. 2, 1959 (1988).
187.L. Forlani, Gazz. Chim. Ital., 121, 475 (1991).
188.L. Forlani and M. Bosi, J. Phys. Org. Chem., 5, 429 (1992).
189.J. Hayami and N. Sugiyama, Proceedings Vth. KISPOC, Japan, 1993, p. 031.
190.N. S. Nudelman and J. Montserrat, J. Chem. Soc., Perkin Trans. 2, 1990, 1073 (1990).
191.H. E. Audier, G. Bouchoux, D. Thilmann, Analysis, 20, 20s (1992).
192.G. Bouchoux, S. Jezequel and F. Penaud Berruyer, Org. Mass. Spectrom, 28, 421 (1993).
193.J. Oszczapowicz, in The Chemistry of Amidines and Imidates (Eds. S. Patai and Z. Rappoport), Vol. 2, Chap. 12, Wiley, Chichester, 1991 and references cited therein.
194.(a) Z. Wu and C. Fenselau, Rapid Commun. Mass Spectrom., 4, 403 (1992).
(b)G. S. Gorman, J. P. Speir, C. A. Turner and I. J. Amster, J. Am. Chem. Soc., 114, 3986 (1992).
195.O. Tapia, R. Cardenas, Y. G. Smeyers, A. Hernandez.Laguna and F. J. Randez, Int. J. Quantum Chem., 38, 727 (1990).
196.A. Hernandez.Laguna, J. L. M. Abboud, R. Notario, H. Homan and Y. G. Smeyers, J. Am. Chem. Soc., 115, 1450 (1993).
197.A. A. Bliznyuk, H. F. Schaefer III and I. J. Amster, J. Am. Chem. Soc., 115, 5149 (1993).
198.R. E. Akpojivi, T. A. Emokpae and J. Hirst, J. Chem. Soc., Perkin Trans. 2, 443 (1994).
199.T. A. Emokpae, P. U. Uwakwe and J. Hirst, J. Chem. Soc., Perkin Trans. 2, 125 (1993).
200.T. A. Emokpae, J. Hirst and P. U. Uwakwe, J. Chem. Soc., Perkin Trans. 2, 2191 (1990).
201.F. Hibbert and J. Emsley, Adv. Phys. Org. Chem., 26, 255 (1990).