Surprising isomer effect in Knoevenagel condensations: Ortho isomer yields polymer and meta isomer yields cyclomer

Macromolecules

Volumn 30, Issue 5, 1997, Pages 1515-1517

  Chafin, A ^a   Lindsay, G ^a   Merwin, L ^a   Ostrom, G ^a   Stenger Smith, J ^a  

^a NAVAL AIR WARFARE CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC POLYMERS; CONFORMATIONS; NITROGEN COMPOUNDS; POLYMERIZATION; XYLENE;

ISOMER EFFECT; KNOEVENAGEL CONDENSATION;

CONDENSATION REACTIONS;

EID: 0031101703     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma951530w     Document Type: Article

References (13)

1. Burland, D. M.; Miller, R. M.; Walsh, C. A. Chem. Rev. 1994, 94, 31-75.
2. Lindsay, G. A. Stenger-Smith, J. D.; Henry, R. A.; Hoover, J. M.; Nissan, R. A.; Wynne, K. J. Macromolecules 1992, 25(22), 6075.
3. J. D. Stenger-Smith, R. A. Henry, A. P. Chefin, L. H. Merwin, R. A. Nissan, R. Y. Yee, M. P. Nadler, G. A. Lindsay, L. M. Hayden, S. Brower, N. Mokal, D. Kokron, W. N. Herman, P. Ashley, Polymers for Second-Order Nonlinear Optics: Lindsay, G. A., Singer, K. D., Eds., Am. Chem. Soc. Symposium Series 601, 1994, pp 181.
4. J. D. Stenger-Smith, R. A. Henry, J. M. Hoover, G. A. Lindsay, M. P. Nadler, R. A. Nissan, J. Polym. Sci.: Part A: Polym. Chem. 1983, 31, 2899.
5. G. A. Lindsay, J. D. Stenger-Smith, R. A. Henry, R. A. Nissan, A. P. Chafin, W. N. Herman and L. M. Hayden, Polym. Prepr. 1993, 34(1), 796.
6. J. H. Kim, F. S. Tham, J. A. Moore, Macromolecules 1993, 26, 2679.
7. Y. Zhang, T. Wada, H. Sasabe, Tetrahedron Lett. 1996, 37(33), 5909-5912.
8. J. S. Dewar, E. G. Zoebisch, E. F. Healy J. J. P. Stewart, J. Am. Chem. Soc. 1985, 107(13), 3902-3909.
9. J. J. P. Stewart, J. Comput. Chem. 1989, 10(2), 221-264.
10. All MOPAC calculations were performed on a Cray-C916 using MOPAC v 6.00. Optimizations were performed using the eigenvector following ("EF") option with all coordinates except nitrile nitrogen dihedrals were marked for optimization.
11. W. J. Hehre, R. Ditchfield, L. Random, J. A. Pople J. Am. Chem. Soc. 1970, 92(16), 4796.
12. S. Penczek, P. Kubisa, K. Matyjaszewski Adv. Polym. Sci 1990, 63, 17.
13. E. J. Goethals Adv. Polym. Sci 1976, 23, 124.