Orthoquinone monoketal chemistry. Experimental and density functional theory studies on orthoquinol acetate rearrangements

Tetrahedron Letters

Volumn 40, Issue 4, 1999, Pages 615-618

  Quideau, Stéphane ^a   Looney, Matthew A ^a   Pouységu, Laurent ^a,b   Ham, Sihyun ^a,c   Birney, David M ^a  

^a TEXAS TECH UNIVERSITY   (United States)

^b UNIVERSITÉ DE BORDEAUX   (France)

^c UNIVERSITY OF WASHINGTON   (United States)

Author keywords

Dimerization; Oxidation; Quinonoid compounds; Rearrangements

Indexed keywords

6 ACETOXY 6 METHOXY 3 METHOXYCARBONYLCYCLOHEXA 2,4 DIENONE; 6,6 DIOXOCYCLOHEXA 2,4 DIEN 1 ONE DERIVATIVE; ACETAL DERIVATIVE; ORTHOQUINOL ACETATE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DIMERIZATION; ENERGY; EPOXIDATION; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS; TEMPERATURE;

EID: 0033593531     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02448-4     Document Type: Article

References (19)

1. Swenton, J. S. Chemistry of Quinone bis- and monoketals. In The Chemistry of Quinonoid Compounds; Patai, S.; Rappoport, Z., Eds.; Wiley: New York, Vol. II, Part 2, 1988, pp. 899-962, and references cited therein.
2. Andersson, G. Acta Chem. Scand. 1976, B 30, 64-70.
3. Miller, B. Rearrangements of Cyclohexadienones. In Mechanisms of Molecular Migrations; Thyagarajan, B. S., Ed.; Wiley: New York, Vol. 1, 1968, pp. 247-313, and references cited therein.
4. Carlini, R.; Higgs, K.; Rodrigo, R.; Taylor, N. Chem. Commun. 1998, 65-66, and references cited therein.
5. Lai, C.-H.; Shen, Y.-L.; Liao, C.-C. Synlett 1997, 1351-1352, and references cited therein.
6. Coleman, R. S.; Grant, E. B. J. Am. Chem. Soc. 1995, 117, 10889-10904.
7. Quideau, S.; Pouységu, L.; Looney, M. A.; Hendley, R. T. Abstracts of Papers, 216th National Meeting of the American Chemical Society, Boston, MA; American Chemical Society: Washington, DC, 1998, ORGN 564.
8. Isolation/purification of compounds were performed by silica gel chromatography, eluting with hexanes-EtOAc (4:1 → 1:1).
9. 10: C, 56.59; H, 5.70. Found: C, 56.39; H, 5.83.
10. Wessely, F.; Swoboda, J.; Guth, V. Monatsh. Chem. 1964, 95, 649-670, and previous papers in the same series.
11. 6: C, 54.99; H, 5.04. Found: C, 54.77; H, 4.99. This material was used without further purification.
12. Adam, W.; Smerz, A. K. J. Org. Chem. 1996, 61, 3506-3510.
13. +) 241.0712, found 241.0708.
14. Zbiral, E.; Saiko, O.; Wessely, F. Monatsh. Chem. 1964, 95, 533-534, and previous papers in the same series.
15. Wessely, F.; Metlesics, W. Monatsh. Chem. 1954, 85, 637-653
16. Woodward, R. B.; Hoffmann, R. Angew. Chem. Int. Ed. Engl. 1969, 8, 781-852.
17. (a) MP4/6-31G**/MP2/6-31G** + ZPE;
18. (b) Birney, D. M.; Xu X.; Ham, S. Angew. Chem. Int. Ed. Engl. 1999, in press.
19. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94, Revision E.2, Gaussian, Inc., Pittsburgh PA, 1995.