S. Le ꢀs niak et al. / Tetrahedron 69 (2013) 722e729
729
spectrometer. The in situ generated compounds were then continu-
ously and simultaneously analyzed by UV-photoelectron
spectrometer.
22. Alcaide, B.; Martin-Cantalejo, Y.; Perez-Castells, J.; Rodriguez-Lopez, J.; Sierra,
M. A.; Monge, A.; P eꢀ rez-Garcia, V. J. Org. Chem. 1992, 57, 5921e5931.
2
2
3. Lesniak, S.; Chrostowska, A.; Kuc, D.; Maciejczyk, M.; Khayar, S.; Nazarski, R. B.;
Urbaniak, q. Tetrahedron 2009, 65, 10581e10589.
4. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman,
J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Car-
icato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg,
J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Naka-
jima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J.
E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.;
Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S.
S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, N. J.; Klene, M.; Knox, J. E.; Cross, J. B.;
Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.;
Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.;
Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels,
Acknowledgements
A.C. and T.Y.V. thank the Agence Universitaire de la Franco-
phonie Asie-Pacifique for PhD financial support. The authors thank
P. Bayl eꢁ re for his efficient technical assistance.
Supplementary data
€
A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09,
Revision A.1; Gaussian: Wallingford CT, 2009.
Calculated geometrical parameters of (E,E)-N-tert-butyl-1-aza-
,3-pentadien N-tert-butyl-(E)-crotonaldimine, 1,4-di-(tert-butyl)-
,4-diazabuta-1,3-dien, 1-tert-butyl-1,3-diazadiene, 1,3-diazadiene,
2
5. (a) Parr, R. G.; Yang, W. Functional Theory of Atoms and Molecules; Oxford
University: New York, 1989; (b) Frisch, M. J.; Trucks, G. W.; Cheeseman, J. R. In
Recent Development and Applications of Modern Density Functional Theory,
Theoretical and Computational Chemistry; Semminario, J. M., Ed.; Elsevier:
Amsterdam, Lausanne, New York, Oxford, Shannon, Tokyo, 1996; Vol. 4,
pp 679e707; (c) Limacher, P. A.; Mikkelsen, K. V.; L u€ thi, H. P. J. Chem. Phys.
1
1
2
2
009, 130, 194114-1e194114-7; (d) Kobayashi, R.; Amos, R. D. Chem. Phys. Lett.
006, 420, 106e109; (e) Jacquemin, D.; Perp eꢁ te, E. A.; Scalmani, G.; Frisch, M. J.;
References and notes
Kobayashi, R.; Adamo, C. J. Chem. Phys. 2007, 14, 144105-1e144105-12.
6. (a) Becke, A. D. Physiol. Rev. 1988, 38, 3098e3100; (b) Becke, S. D. J. Chem. Phys.
1993, 98, 5648e5652; (c) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37,
785e789; (d) Yanai, T.; Tew, D.; Handy, N. Chem. Phys. Lett. 2004, 393, 51e57.
2
1. Perez, J. D.; Yranzo, G. I.; Phagouape, L. M. Bull. Soc. Chim. Fr. 1986, 1, 129e132.
2
. Metail, V.; Joanteguy, S.; Chrostowska-Senio, A.; Pfister-Guillouzo, G.; Syster-
mans, A.; Ripoll, J. L. Inorg. Chem. 1997, 36, 1482e1487.
27. (a) Joant eꢀ guy, S.; Pfister-Guillouzo, G.; Chermette, H. J. Phys. Chem. 1999, 103,
3
. Lef eꢁ vre, V.; Ripoll, J. L.; Dat, Y.; Joanteguy, S.; Metail, V.; Chrostowska-Senio, A.;
3505e3511; (b) Chrostowska, A.; Miqueu, K.; Pfister-Guillouzo, G.; Briard, E.;
Levillain, J.; Ripoll, J.-L. J. Mol. Spectrosc. 2001, 205, 323e330; (c) Bartnik, R.;
Bayl eꢁ re, P.; Chrostowska, A.; Galindo, A.; Lesniak, S.; Pfister-Guillouzo, G. Eur. J.
Pfister-Guillouzo, G. Organometallics 1997, 16, 1635e1640.
4
5
. Levillain, J.; Pfister-Guillouzo, G.; Ripoll, J. L. Eur. J. Org. Chem. 2000, 3253e3259.
. Zhang, T.; Zhang, L.; Wang, J.; Yuan, T.; Hong, X.; Qi, F. J. Phys. Chem. A 2008, 112,
Org. Chem. 2003, 13, 2475e2479.
1
0495e10501.
28. (a) Stratmann, R. E.; Scuseria, G. E.; Frisch, M. J. J. Chem. Phys. 1998, 109,
8218e8224; (b) Casida, M. E.; Jamorski, C.; Casida, K. C.; Salahub, D. R. J. Chem.
Phys. 1998, 108, 4439e4449; (c) Lemierre, V.; Chrostowska, A.; Dargelos, A.;
Chermette, H. J. Phys. Chem. A 2005, 109, 8348e8355.
6
7
8
. Mondal, B.; Mandal, D.; Das, A. K. J. Phys. Chem. A 2011, 115, 3068e3078.
. Pacansky, J.; Chang, J. S.; Brown, D. W. Tetrahedron 1982, 38, 257e260.
. Engel, P. S.; Li, P.; Whitmire, K. H.; Guzman-Himenez, J.; Willcot, M. R.; Smith,
W. B. J. Org. Chem. 2000, 65, 1016e1021.
29. (a) von Niessen, W.; Schirmer, J.; Cederbaum, L. S. Comput. Phys. Rep. 1984, 1,
9. McNab, H. J. Chem. Soc., Perkin Trans. 1 1980, 2200e2204.
57e125; (b) Ortiz, J. V. J. Chem. Phys. 1988, 89, 6348e6352.
1
1
1
1
1
1
1
0. Hickson, C. L.; McNab, H. Synthesis 1981, 464e465.
1. McNab, H.; Smith, G. S. J. Chem. Soc., Chem. Commun. 1982, 996e997.
2. Hickson, C. L.; McNab, H. J. Chem. Soc., Perkin Trans. 1 1984, 1569e1572.
3. McNab, H. Aldrichimica Acta 2004, 37, 19e26.
4. Sell, J. A.; Kuppermann, A. Chem. Phys. Lett. 1979, 61, 355e362.
5. Houk, K. N.; Munchausen, L. L. J. Am. Chem. Soc. 1976, 98, 937e946.
6. Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazaki, T.; Iwata, S. Handbook of He I
Photoelectron Spectra of Fundamental Organic Molecules; Japan Scientific: Tokyo,
981; and Ref. cited therein.
7. Lesniak, S. Pol. J. Chem. 1995, 69, 1490e1496.
8. Kajfez, F.; Klasinc, L.; Sunjic, V. J. Heterocycl. Chem. 1979, 16, 529e531.
9. Bellassoued, M.; Salemkour, M. Tetrahedron 1996, 52, 4607e4624.
31. Stowasser, R.; Hoffmann, R. J. Am. Chem. Soc. 1999, 121, 3414e3420.
32. (a) Chrostowska, A.; Dargelos, A.; Graciaa, A.; Bayl eꢁ re, P.; Lee, V. Y.; Naka-
moto, M.; Sekiguchi, A. Organometallics 2008, 27, 2915e2917; (b) Guillemin,
J.-C.; Chrostowska, A.; Dargelos, A.; Nguyen, T. X. M.; Graciaa, A.; Guenot, P.
Chem. Commun. 2008, 35, 4204e4206; (c) Chrostowska, A.; Lemierre, V.;
Dargelos, A.; Bayl eꢁ re, P.; Leigh, W. J.; Rima, G.; Weber, L.; Schimmel, M. J.
Organomet. Chem. 2009, 694, 43e51; (d) Chrostowska, A.; Nguyen, T. X. M.;
Dargelos, A.; Khayar, S.; Graciaa, A.; Guillemin, J.-C. J. Phys. Chem. A 2009,
113, 2387e2396; (e) Chrostowska, A.; Dargelos, A.; Graciaa, A.; Khayar, S.;
Le ꢀs niak, S.; Nazarski, R. B.; Nguyen, T. X. M.; Rachwalski, M. Tetrahedron
1
1
1
1
20. Ledoux, N.; Allaert, B.; Pattyn, S.; Mierde, H. V.; Vercaemst, C.; Verpoort, F.
2009, 65, 9322e9327.
Chem.dEur. J 2006, 12, 4654e4661.
1. Kliegman, J. M.; Barnes, R. K. J. Tetrahedron 1970, 26, 2555e2558.
33. Varetto, U. MOLEKEL Version, Swiss National Supercomputing Centre: Manno,
Switzerland.
2