Synthesis of heteroaryl imines: Theoretical and experimental approach to the determination of the configuration of C=N double bond

Journal of Organic Chemistry

Volumn 71, Issue 19, 2006, Pages 7165-7179

  Amati, Mario ^a   Bonini, Carlo ^b   D'Auria, Maurizio ^b   Funicello, Maria ^b   Lelj, Francesco ^a   Racioppi, Rocco ^b  

^a UNIVERSITY OF BASILICATA   (Italy)

^b Department of Chemistry ^*  (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; IRRADIATION; ISOMERS; MIXTURES; PHOTOCHEMICAL REACTIONS; REACTION KINETICS; SPECTRUM ANALYSIS; STEREOCHEMISTRY;

COMPUTED TRANSITIONS; HETEROARYL IMINES; IMINOPHOSPHORANE; NONPLANAR; THIOPHENE-2-CARBALDEHYDE;

NITROGEN COMPOUNDS;

FURAN DERIVATIVE; FURFURAL; HETEROCYCLIC COMPOUND; IMINE; PHOSPHORANE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; THIOPHENE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CIS TRANS ISOMERISM; CYCLIZATION; ENANTIOMER; ENERGY; EXPERIMENTAL STUDY; ORGANIC CHEMISTRY; STEREOCHEMISTRY; SYNTHESIS; THEORETICAL STUDY; ULTRAVIOLET SPECTROSCOPY;

EID: 33749029650     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0605501     Document Type: Article

References (26)

1. (a) Barluenga, J.; Palacios, F. Org. Prep. Proced. Int. 1991, 1.
2. (b) Golologov, Y. G.; Kausukhin, L. F. Tetrahedron 1992, 48, 1353-1406.
3. (c) Molina, P.; Vilaplana, M. J. Synthesis 1994, 1197-1218.
4. (d) Wamhoff, H.; Richardt, G.; Stolben, S. Adv. Heterocycl. Chem. 1995, 64, 159-249.
5. (e) Funicello, M.; Spagnolo, P. In Targets in Heterotyclic Chemistry; Attanasi, O. A., Spinelli, D., Eds.; Italian Society of Chemistry: Rome, Italy, 2004; Vol. 8. pp 274-287.
6. Degl'Innocenti, A.; Funicello, M.; Scafato, P.; Spagnolo, P.; Zanirato, P. J. Chem. Soc., Perkin Trans. 1 1996, 2561-2563.
7. Bonini, C.; Chiummiento, L.; Funicello, M.; Spagnolo, P. Tetrahedron 2000, 56, 1517-1521.
8. Bonini, C.; D'Auria, M.; Funicello, M.; Romaniello, G. Tetrahedron 2002, 58, 3507-3512.
9. For C=N thermal and/or photochemical isomerization: (a) Curtin, D. Y.; Hausser J. W. J. Am. Chem. Soc. 1961, 83, 3474-3481.
10. (b) Raban, M.; Carlson, E. J. Am. Chem. Soc. 1971, 93, 685-691.
11. (c) Marcoccia, J. F.; Yates, K.; Csizmadia, I. G. J. Mol. Struct. (THEOCHEM) 1996, 360, 1-39.
12. (d) Padwa, A. Chem. Rev. 1977, 77, 37-68.
13. (e) Stepanenko, T.; Lapinski, L.; Sobolewski, A. L.; Nowak, M. J.; Kierdaszuk, B. J. Phys. Chem. A 2000, 104, 9459-9466.
14. (f) King, N. R.; Whale, E. A.; Davis, F. J.; Gilbert, A.; Mitchell, G. R. J. Mater. Chem. 1997, 7, 625-630.
15. (g) Johnson, J. E.; Morales, N. M.; Gorczyca, A. M.; Dolliver, D. D.; McAllister M. A. J. Org. Chem. 2001, 66, 7979-7985.
16. (a) Paetzold, R.; Reichenbacher, M.; Appenroth, K. Z. Chem. 1981, 21, 421-430.
17. (b) Bonǎcić-Koutecký, V.; Michl, J. Theor. Chim. Acta 1985, 68, 45-55.
18. Stepanenko, T.; Lapinski, L.; Nowak, M. J.; Adamowicz, L. Vib. Spectrosc. 2001, 26, 65-82.
19. Parr, R. G.; Yang, W. Density Functional Theory of atoms and molecules; Oxford University Press: New York; Clarendon Press: Oxford, 1989.
20. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
21. Casida, M. E. In Recent Advances in Density Functional Methods; Chong, D. P., Ed.; World Scientific: Singapore, 1995; Vol. 1, pp 155-192.
22. Casida, M. E.; Jamorski, C.; Casida, K. C.; Salahub, D. R. J. Chem. Phys. 1998, 108, 4439-4449.
23. Becke, A. D. Phys. Rev. A 1988, 38, 3098-3100.
24. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
25. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.11; Gaussian, Inc.: Pittsburgh, PA, 2001.
26. Schaftenaar, G.; Noordik, J. H. J. Comput.-Aided Mol. Des. 2000, 14, 123-134 (http://www.cmbi.ru.nl/molden/molden.html).