LFER Correlation of 13C Chemical Shift in Para-Substituted Phenyl Isocyanide: Implications for Formation of a Unique Polymer

Journal of Organic Chemistry

Volumn 62, Issue 11, 1997, Pages 3766-3769

  Kim, Misoo ^a   Euler, William B ^a   Rosen, William ^a  

^a University of Rhode Island   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000582854     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961494e     Document Type: Article

References (23)

1. Hammett, L. P. J. Am. Chem. Soc. 1937, 59, 96.
2. Craik, D. J.; Brownlee, R. T. C. Prog. Phys. Org. Chem. 1983, 14, 1.
3. Huang, J.-T.; Sun, J.; Euler, W. B.; Rosen, W. J. Polym. Sci., Part A, Polym. Chem. 1997, 35, 439.
4. Nolte, R. J. M.; Drenth, W. New Methods for Polymer Synthesis; Mijs, W. J., Ed.; Plenum Press: New York, 1992; p 273.
5. Ugi, I.; Fetzer, U.; Eholzer, U.; Knupper, H.; Offerman, K. Angew. Chem. Int. Ed. Eng. 1965, 4, 472.
6. New, R. G. A.; Sutton, L. E. J. Chem. Soc. 1932, 1415. Ugi, I.; Meyr, R. Chem. Ber., 1960, 93, 239; King, R. B.; Greene, M. J. J. Polym. Sci., Part A, Polym. Chem., 1987, 25, 907.
7. New, R. G. A.; Sutton, L. E. J. Chem. Soc. 1932, 1415. Ugi, I.; Meyr, R. Chem. Ber., 1960, 93, 239; King, R. B.; Greene, M. J. J. Polym. Sci., Part A, Polym. Chem., 1987, 25, 907.
8. New, R. G. A.; Sutton, L. E. J. Chem. Soc. 1932, 1415. Ugi, I.; Meyr, R. Chem. Ber., 1960, 93, 239; King, R. B.; Greene, M. J. J. Polym. Sci., Part A, Polym. Chem., 1987, 25, 907.
9. Fieser, L. F.; Fieser, M. Reagents Org. Synth. 1967, 1, 4. Krimen, L. I. Organic Synthesis; Noland, W. E., Ed.; John Wiley & Sons: New York, 1988; Collect, Vol. VI, p 8.
10. Fieser, L. F.; Fieser, M. Reagents Org. Synth. 1967, 1, 4. Krimen, L. I. Organic Synthesis; Noland, W. E., Ed.; John Wiley & Sons: New York, 1988; Collect, Vol. VI, p 8.
11. Skorna, G.; Ugi, I. Angew. Chem. Int. Ed. Engl. 1977, 16, 259.
12. Juchnovski, I. N.; Tsenov, J. A. Spectrosc. Lett. 1995, 28, 211.
13. Corey, E. J.; Snider, B. B. J. Am. Chem. Soc. 1972, 94, 2549.
14. Ugi, I. Isonitrile Chemistry; Academic Press, New York, 1971.
15. Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165.
16. Stephany, R. W.; de Bie, M. J. A.; Drenth, W. Org. Magn. Reson. 1974, 6, 45.
17. Topsom, R. D. Prog. Phys. Org. Chem. 1987, 16, 125.
18. This less intense, high-energy shoulder may be due to a Fermi resonance, as implied in ref 9. We did not pursue this explanation further as 3k was the only example that showed this phenomenon. Another explanation might be that the shoulder could be associated with the proposed equilibrium that involved structure 31.
19. Ferris, J. P.; Antonucci, F. R.; Trimmer, R. W. J. Am. Chem. Soc. 1973, 95, 919.
20. Jutzi, P.; Gilge, U. J. Organomet. Chem. 1983, 246, 159.
21. Fraser, R. R.; Mansour, T. S.; Savard, S. Can. J. Chem. 1985, 63, 3505.
22. 1H NMR time scale.
23. LaPlanehe, L. A.; Rogers, M. T. J. Am. Chem. Soc. 1964, 86, 337.