Derivative of α,β-dicyanostilbene: Convenient precursor for the synthesis of diphenylmaleimide compounds, E-Z isomerization, crystal structure, and solid-state fluorescence

Journal of Organic Chemistry

Volumn 69, Issue 19, 2004, Pages 6455-6462

  Yeh, Hsiu Chih ^a   Wu, Wei Ching ^a   Wen, Yuh Sheng ^a   Dai, De Chang ^a   Wang, Juen Kai ^b,c   Chen, Chin Ti ^a  

^a INSTITUTE OF CHEMISTRY   (Taiwan)

^b NATIONAL TAIWAN UNIVERSITY   (Taiwan)

^c INSTITUTE OF ATOMIC AND MOLECULAR SCIENCES   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; CRYSTAL STRUCTURE; DERIVATIVES; ISOMERIZATION; PURIFICATION; SINGLE CRYSTALS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL); X RAY ANALYSIS;

FUMARONITRILE; MALEIMIDE COMPOUNDS; PHENYLACETONITRILE COMPOUNDS; SINGLE-CRYSTAL X-RAY STRUCTURES;

NITROGEN COMPOUNDS;

ALPHA,BETA DICYANOSTILBENE; BENZYL CYANIDE DERIVATIVE; BIS(3 TRIFLUOROMETHYLPHENYL)FUMARONITRILE; BIS(4 BROMOPHENYL)FUMARONITRILE; BIS(4 METHOXYPHENYL)FUMARONITRILE; DIPHENYLMALEIMIDE DERIVATIVE; MALEIMIDE DERIVATIVE; METHOXIDE SODIUM; STILBENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; FILTRATION; FLUORESCENCE; ISOMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; SOLID STATE; STOICHIOMETRY; SYNTHESIS;

EID: 4644222153     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049512c     Document Type: Article

References (29)

1. Yeh, H.-C.; Chan, L.-H.; Wu, W.-C.; Chen, C. T. J. Mater. Chem. 2004, 14, 1293.
2. For examples see (a) Chalanay, L.; Knoevenagel, E. Chem. Ber. 1892, 25, 285.
3. (b) Heller, G. Justus Liebigs Ann. Chem. 1904, 332, 247.
4. (c) Cook, A. H.; Linstead, R. P. J. Chem. Soc. 1937, 929.
5. (d) Koelsch, C. F.; Wawzonek, S. J. Org. Chem. 1941, 6, 684.
6. (e) Niederl, J.; Ziering, A. J. Am. Chem. Soc. 1942, 64, 2486.
7. (f) Weizman, M.; Patai, S. J. Am. Chem. Soc. 1949, 71, 2587.
8. (g) Coe, D. G.; Gale, M. M.; Linstead, R. P.; Timmons, C. J. J. Chem. Soc. 1957, 123 and refs 1-11 cited therein for the synthesis of dipehenylfumaronitrile in the late 19th and early 20th centuries.
9. (h) Marinina, L. E.; Mikhalenko, S. A.; Luk'yanets, E. A. J. Gen. Chem. USSR 1974, 43, 2010.
10. (i) Irie, M.; Mohri, M. J. Org. Chem. 1988, 53, 803.
11. (j) Fields, E. K.; Behrend, J.; Meyerson, S.; Winzenburg, M. L.; Ortega, B. R.; Hall, H. K., Jr. J. Org. Chem. 1999, 55, 5156.
12. (k) Hanack, M.; Renz, G. Chem. Ber. 1990, 123, 1105.
13. (l) Baumann, T. F.; Barrett, A. G. M.; Hoffman, B. M. Inorg. Chem. 1997, 36, 5661.
14. (m) Anderson, M. E.; Barrett, A. G. M.; Hoffman, B. M. Inorg. Chem. 1999, 38, 6143.
15. (n) Meyers, M. J.; Sun, J.; Carlson, K. E.; Marriner, G. A.; Katzenellenbogen, B. S.; Katzenellenbogen, J. A. J. Med. Chem. 2001, 44, 4230.
16. (o) Vagin, S. I.; Hanack, M. Eur. J. Org. Chem. 2002, 2859.
17. (p) Vagtin, S.; Barthel, M.; Dini, D.; Hanack, M. Inorg. Chem. 2003, 42, 2683.
18. Wu, W.-C.; Yeh, H.-C.; Chan, L.-H.; Chen, C.-T. Adv. Mater. 2002, 14, 1072.
19. Yeh, H.-C.; Yeh, S.-J.; Chen, C.-T. Chem. Commun. 2003, 2632.
20. Yeh, H.-C.; Wu, W.-C.; Chen, C.-T. Chem. Commun. 2003, 404.
21. (a) Baguley, M. E.; France, H.; Linstead, R. P.; Whalley, M. J. Chem. Soc. 1955, 3521.
22. (b) Fitzgerald, J.; Tayloer, W.; Owen, H. Synthesis 1991, 686.
23. (c) The base sensitivity of the isomerization of fumaronitrile and maleonitrile has been noted again recently (Huisgen, R.; Li, X.; Giera, H.; Langhals E. Helv. Chim. Acta 2001, 84, 981). The central C-C double bond of either fumaronitrile or maleonitrile is susceptible to base, such as fluoride, alkoxide, or even a polar solvent molecule such as acetonitrile. It is conceivable that the base acts as a nucluophile in transforming the double bond to a rotary C-C single bond. The C-C double bond can thus be recovered after the elimination of the substituted base but with alternative isomer structure (from cis to trans form or from trans to cis form).
24. Wallwork, S. C. Acta Crystallogr. 1961, 14, 375.
25. Costain, C. C.; Stoicheff, B. P. J. Chem. Phys. 1959, 30, 777.
26. Hoekstra, A.; Meertens, P.; Vos, A. Acta Crystallogr., Sect. B 1975, 31, 2813.
27. Faulmann, C.; Cassoux, P.; Pullen, A. E. Acta Crystallogr., Sect. B 2000, 56, 384.
28. Gluster, J. P.; Lewis, M.; Rossi, M. Crystal Structure Analysis for Chemists and Biologists; VCH: Weinheim, Germany, 1994.
29. de Mello, J. C.; Wittmann, H. F.; Friend, R. H. Adv. Mater. 1997, 9, 230.