Photooxidation of methylnaphthalenes

Journal of Organic Chemistry

Volumn 70, Issue 1, 2005, Pages 105-109

  Wasserman, Harry H ^a   Wiberg, Kenneth B ^a   Larsen, David L ^a   Parr, Jonathan ^a  

^a YALE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARRIER CONCENTRATION; PEROXIDES; PHOTOOXIDATION; REACTION KINETICS; STABILITY;

ENDOPEROXIDE; ENERGETICS; METHYLNAPTHALENES; STERIC INTERACTIONS;

NAPHTHALENE;

1,2,3,4 TETRAMETHYLNAPHTHALENE; 1,2,3,4 TETRAMETHYLNAPHTHALENE 1,4 ENDOPEROXIDE; 1,2,4 TRIMETHYLNAPHTHALENE 1,4 ENDOPEROXIDE; 1,4 DIMETHYLNAPHTHALENE; 1,4 DIMETHYLNAPHTHALENE 1,4 ENDOPEROXIDE; 1,4,5 TRIMETHYLNAPHTHALENE 1,4 ENDOPEROXIDE; 1,8 DIMETHYLNAPHTHALENE; 1,8 DIMETHYLNAPHTHALENE 1,4 ENDOPEROXIDE; AROMATIC HYDROCARBON; ENDOPEROXIDE; METHYL GROUP; NAPHTHALENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; CHEMICAL REACTION; DENSITY; ELECTRON; ENERGY TRANSFER; MOLECULAR STABILITY; PHOTOOXIDATION; STEREOSPECIFICITY;

EID: 11844294659     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo040228v     Document Type: Article

References (29)

1. (a) Aubry, J.-M.; Pierlot, C.; Rigaudy, J.; Schmidt, R. Acc. Chem. Res. 2003, 36, 668-675.
2. (b) Gollnick, K. Adv. Photochem. 1968, 6, 1-122.
3. (c) Gollnick, K.; Schenck, G. O. Oxygen as a Dienophile. In 1,4-Cycloadition Reactions; Hamer, J., Ed.; Academic Press: New York, 1967; pp 255-344.
4. (d) Baldwin, J. E.; Basson, H. H.; Krauss, H., Jr. Chem. Commun. 1968, 984-985.
5. (e) Rigaudy, J.; Dupont, R.; Cuong, N. K. C. R. Acad. Sci. 1969, 269c, 416-419.
6. (f) Wilson, R. Photochem. Photobiol. 1969, 10, 441-449.
7. (g) Rigaudy, J.; Guillaume, J.; Maurette, D. Bull. Soc. Chim. Fr. 1971, 144-152.
8. (h) Saito, I.; Matsuura, T. In Singlet Oxygen; Wasserman, H. H., Murray, R. W., Eds.; Academic Press: New York, 1979; Vol. 40, pp 511-569.
9. (a) Rigaudy, J.; Deletang, C.; Basselier, J.-J. C. R. Acad. Sci. 1966, 263c, 1435-1438.
10. (b) Rigaudy, J. Pure Appl. Chem. 1968, 16, 169-186.
11. (c) Rigaudy, J.; Deletang, C.; Sparfel, D.; Cuong, N. K. C. R. Acad. Sci. 1968, 267c, 1714-1717.
12. (d) Rigaudy, J.; Deletang, C.; Basselier, J.-J. C. R. Acad. Sci. 1969, 268c, 344-347.
13. (a) Wasserman, H. H.; Larsen, D. L. Chem. Commun. 1972, 253-254.
14. (b) Larsen, D. L. Ph.D. Thesis, Yale University, New Haven, CT, 1973.
15. Many of the naphthalene endoperoxides prepared in this work (Table 1) show little evidence of decomposition after several months storage at 0°C.
16. Yew, F. F.; Kurland, R. J.; Mair, B. J. Anal. Chem. 1964, 36, 843-845.
17. It is noteworthy that octamethylnaphthalene-1,4-endoperoxide is inert to both sodium borohydride and lithium aluminium hydride. See: Hart, H.; Oku, A. Chem. Commun. 1972, 254-255.
18. Hydrogenation of 1,4-dimethylnaphthyl-1,4-endoperoxide in the presence of a platinum catalyst gives 1,4-dihydroxy-1,4-dimethyl-1,2,3,4- tetrahydronaphthalene exclusively. See: Rigaudy, J.; Maurette, D.; Cuong, N. K. C. R. Acad. Sci. 1971, 273c, 1553-1556.
19. Singlet Oxygen; Wasserman, H. H., Murray, R. W., Eds.; Academic Press: New York, 1979; Vol. 40.
20. (a) van den Huevel, C. J. M.; Steinberg, H.; de Boer, Th. J. Recl. Trav. Chim. Pays-Bas. 1980, 99, 109-113.
21. (b) van den Huevel, C. J. M.; Verhoeven, J. W.; de Boer, Th. J. Recl. Trav. Chim. Pays-Bas. 1980, 99, 280-284.
22. The influence of peri interactions on the chemistry of naphthalenes has been reviewed. See: Balasubramaniyan, V. Chem. Rev. 1966, 66, 567-641.
23. The C1-C8 distance in naphthalene is 2.44 Å, the C1-C8A bond length is 1.42 Å and the C1-C8A-C8 angle is slightly larger than 120°. See: Cruickshank, D. W. J. Acta Crystallogr. 1957, 10, 504-508.
24. The total energies, zero-point energies, and changes in enthalpy and free energy are available as Supporting Information.
25. In comparing 1,8- and 1,5-dimethylnaphthalene, the latter cannot be taken as strain-free as there are methyl-hydrogen peri interactions that, although probably small, cannot be neglected. The heats of formation of 1- and 2-methylnaphthalenes as reported by Rossini differ somewhat (Speros, D. M.; Rossini, F. D. J. Phys. Chem. 1960, 64, 1723-1727). On the basis of error limits for this determination, the strain energy for a 1-methyl to 8-hydrogen interaction lies between zero and 900 cal/mol. Thus, two such interactions as in the case of 1,5-dimethylnaphthalene could result in a total strain energy of 1.8 kcal/mol, which when combined with the probable differences between the 1,5- and 1,8-isomers implies that the strain associated with a peri methyl-methyl interaction may be as great as 7.3 kcal/ mol. The results of Packer indicate that the strain in 1-methylnaphthalene, 1,2-dimethylnaphthalene, and 1,8-dimethylnaphthalene may be 1.6, 3.4, and 7.6 kcal/mol, respectively ( Packer, J.; Vaughan, J.; Wong, E. J. Am. Chem. Soc. 1958, 80, 905-907). Although the arguments of Packer et al. are not conclusive, these values may be quite close to being correct.
26. In comparing 1,8- and 1,5-dimethylnaphthalene, the latter cannot be taken as strain-free as there are methyl-hydrogen peri interactions that, although probably small, cannot be neglected. The heats of formation of 1- and 2-methylnaphthalenes as reported by Rossini differ somewhat (Speros, D. M.; Rossini, F. D. J. Phys. Chem. 1960, 64, 1723-1727). On the basis of error limits for this determination, the strain energy for a 1-methyl to 8-hydrogen interaction lies between zero and 900 cal/mol. Thus, two such interactions as in the case of 1,5-dimethylnaphthalene could result in a total strain energy of 1.8 kcal/mol, which when combined with the probable differences between the 1,5- and 1,8-isomers implies that the strain associated with a peri methyl-methyl interaction may be as great as 7.3 kcal/ mol. The results of Packer indicate that the strain in 1-methylnaphthalene, 1,2-dimethylnaphthalene, and 1,8-dimethylnaphthalene may be 1.6, 3.4, and 7.6 kcal/mol, respectively ( Packer, J.; Vaughan, J.; Wong, E. J. Am. Chem. Soc. 1958, 80, 905-907). Although the arguments of Packer et al. are not conclusive, these values may be quite close to being correct.
27. It should be noted that the ΔH values are somewhat more reliable than ΔG values because the latter is influenced by changes in methyl rotational barriers that were not explicitly calculated in this study.
28. Shangguan, C.; McAllister, M. A. J. Mol. Struct. 1998, 422, 123-132.
29. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E. Robb, M. A.; Cheeseman, J. R.; Zakrewski, 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.; Malik, D. K.; Rabuck, A. D.; Raghavachari, K. Foresman, J. B.; Ortiz, J. V.; Baboul, A. G.; Cioslowski, J.; 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.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 99, Development Version (Rev. B.04); Gaussian, Inc., Pittsburgh, PA, 1998.