Monbaliu, Jean-Christophe ; Université Catholique de Louvain – UCL > Institute of Condensed Matter and Nanosciences > Molecules, Solids and Reactivity (MOST)
Marchand-Brynaert, Jacqueline; Université Catholique de Louvain – UCL > Institute of Condensed Matter and Nanosciences > Molecules, Solids and Reactivity (MOST)
Peeters, Daniel; Université Catholique de Louvain – UCL > Institute of Condensed Matter and Nanosciences > Molecules, Solids and Reactivity (MOST)
Language :
English
Title :
Is anthracene cofactor or spectator for the thermolysis of anthracenyl acylnitroso cycloadducts in the presence of a diene?
Cohen A., Zeng B., King S., and Toscano J. J. Am. Chem. Soc. 125 (2003) 1444-1445
Kirby G. Chem. Soc. Rev. 6 (1977) 12-22
Corrie J., Kirby G., and Mackinnon J. J. Chem. Soc., Perkin Trans. 1 (1985) 883-886
Kirby G., and Mackinnon J. J. Chem. Soc., Perkin Trans. 1 (1985) 887-892
Kirby G., Mcguigan H., and Mclean D. J. Chem. Soc., Perkin Trans. 1 (1985) 1961-1966
Christie C., Kirby G., Mcguigan H., and Mackinnon J. J. Chem. Soc., Perkin Trans. 1 (1985) 2469-2473
Corrie J., Kirby G., and Sharma R. J. Chem. Soc., Perkin Trans. 1 (1982) 1571-1572
Kirby G., and Sweeny J. J. Chem. Soc., Perkin Trans. 1 (1981) 3250-3254
Horsewood P., Kirby G., Sharma R., and Sweeny J. J. Chem. Soc., Perkin Trans. 1 (1981) 1802-1806
Ganga V.B., Sreeja T., Suresh E., and Varma R.L. Tetrahedron 63 (2007) 4134-4143
Bodnar B.S., and Miller M.J. J. Org. Chem. 72 (2007) 3929-3932
Adam W., and Krebs O. Chem. Rev. 103 (2003) 4131-4146
Yamamoto H., and Kawasaki M. Bull. Chem. Soc. Jpn. 80 (2007) 595-607
Yamamoto Y., and Yamamoto H. Eur. J. Org. Chem. (2006) 2031-2043
Yamamoto Y., and Yamamoto H. Angew. Chem., Int. Ed. 44 (2005) 7082-7085
Zhu L., Lauchli R., Loo M., and Shea K.J. Org. Lett. 9 (2007) 2269-2271
Kibayashi C., Aoyagi S., and Abe H. J. Synth. Org. Chem. Jpn. 65 (2007) 805-819
Fokin A.A., Yurchenko A.G., Rodionov V.N., Gunchenko P.A., Yurchenko R.I., Reichenberg A., Wiesner J., Hintz M., Jomaa H., and Schreiner P.R. Org. Lett. 9 (2007) 4379-4382
Jiang M.X., Jin B., Gage J.L., Priour A., Savela G., and Miller M.J. J. Org. Chem. 71 (2006) 4164-4169
Li F., Warshakoon N., and Miller M. J. Org. Chem. 69 (2004) 8836-8841
Iwasa S., Fakhruddin A., and Nishiyama H. Mini-Rev. Org. Chem. 2 (2005) 157-175
Streith J., and Defoin A. Synthesis (1994) 1107-1117
Defoin A., Fritz H., Schidlin C., and Streith J. Helv. Chim. Acta 70 (1987) 554-569
Boger D.L., Patel M., and Takusagawa F. J. Org. Chem. 50 (1985) 1911-1916
Adamo M.F.A., and Bruschi S. J. Org. Chem. 72 (2007) 2666-2669
Chow C., and Shea K. J. Am. Chem. Soc. 127 (2005) 3678-3679
Quadrelli P., Mella I., Carosso S., Bovio B., and Caramella P. Eur. J. Org. Chem. (2007) 6003-6015
Quadrelli P., Invernizzi A., and Caramella P. Tetrahedron Lett. 37 (1996) 1909-1912
Keck G., Webb R., and Yates J. Tetrahedron 37 (1981) 4007-4016 See also Ref.4
Atherton J., and Jones S. Tetrahedron 59 (2003) 9039-9057
Chung Y., Duerr B., Mckelvey T., Nanjappan P., and Czarnik A. J. Org. Chem. 54 (1989) 1018-1032
Manoharan M., De Proft F., and Geerlings P. J. Chem. Soc., Perkin Trans. 2 (2000) 1767-1773
Kitamura T., Yamane M., Inoue K., Todaka M., Fukatsu N., Meng Z., and Fujiwara Y. J. Am. Chem. Soc. 121 (1999) 11674-11679
Leach A., Houk K., and Reymond J. J. Org. Chem. 69 (2004) 3683-3692
X-ray data for several acylnitroso anthracenyl cycloadducts show unprecedented N-O bond length (1.48 Å instead of 1.41 Å as observed in classical 3,4-dihyro-1,2-oxazine patterns). This enhancement of the N-O bond length can also be interpreted as a consequence of a reduced bond order for the oxazine bond (i.e., it suggests both activation of the oxygen and the nitrogen atoms). Chen W., Day C.S., and King S.B. J. Org. Chem. 71 (2006) 9221-9224
Kirby G., Mcguigan H., Mackinnon J., Mclean D., and Sharma R. J. Chem. Soc., Perkin Trans. 1 (1985) 1437-1442
Liu X., and Snyder J.K. J. Org. Chem. 73 (2008) 2935-2938
Adams H., Bawa R.A., McMillan K.G., and Jones S. Tetrahedron: Asymmetry 18 (2007) 1003-1012
Adams H., Bawa R.A., and Jones S. Org. Biomol. Chem. 4 (2006) 4206-4213
Adams H., Jones S., and Ojea-Jimenez I. Org. Biomol. Chem. 5 (2006) 2296-2303
Sasaoka A., Uddin M.I., Shimomoto A., Ichikawa Y., Shiro M., and Kotsuki H. Tetrahedron: Asymmetry 17 (2006) 2963-2969
Burgess K., Lajkiewicz N., Sanyal A., Yan W., and Snyder J. Org. Lett. 7 (2005) 31-34
Sanyal A., Yuan Q., and Snyder J. Tetrahedron Lett. 46 (2005) 2475-2478
Burgess K., Corbett M., Eugenio P., Lajkiewicz N., Liu X., Sanyal A., Yan W., Yuan Q., and Snyder J. Bioorg. Med. Chem. 13 (2005) 5299-5309
Monbaliu J.-C., and Marchand-Brynaert J. Tetrahedron Lett. 49 (2008) 1839-1842
Robiette R., Defacqz N., Peeters D., and Marchand-Brynaert J. Curr. Org. Synth. 2 (2005) 453
Robiette R., Marchand-Brynaert J., and Peeters D. J. Mol. Struct. (THEOCHEM) 587 (2002) 159-169
Reaction with acetylnitroso 3 is strongly exothermic (ΔG = -48.3 kcal mol-1) because the final product is an amide rather than an amine, as for MeNO 2 (ΔG=-28.2 kcal mol-1).
For the formation of 8 (R1 = Ac), ΔG = -18.2 kcal mol-1. For the formation of 7 (R1 = Me), ΔG = -0.6 kcal mol-1. See also note 20.
Birney D., Lim T., Koh J., Pool B., and White J. J. Am. Chem. Soc. 124 (2002) 5091-5099
Pool B., and White J. Org. Lett. 2 (2000) 3505-3507
For butadiene, this cisoid-transoid equilibrium costs about 2 kcal mol-1, as the HD-A process with acetylnitroso 3.
Becke A. J. Chem. Phys. 98 (1993) 5648-5652
Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Zakrzewski V.G., Montgomery J.J.A., 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., Baboul A.G., 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., Chen W., Wong M.W., Andres J.L., Gonzalez C., Head-Gordon M., Replogle E.S., and Pople J.A. Gas Phase Calculations Were Done Using the Gaussian Suite of Programs, Revision A.7 (1998), Gaussian, Pittsburgh PA
Gonzalez C., and Schlegel H.B. J. Chem. Phys. 94 (1990) 5523-5527
Gonzalez C., and Schlegel H.B. J. Chem. Phys. 4 (1989) 2154-2161
Reed A.E., Weinstock F., and Weinhold F. J. Chem. Phys. 83 (1985) 735-746
