Oxatriquinane and oxatriquinacene: Extraordinary oxonium ions

Journal of the American Chemical Society

Volumn 130, Issue 41, 2008, Pages 13532-13533

  Mascal, Mark ^a   Hafezi, Nema ^a   Meher, Nabin K ^a   Fettinger, James C ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

OXATRIQUINACENE; OXATRIQUINANE; OXYGEN; TRICYCLIC AROMATIC COMPOUND; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG; ZINC CHLORIDE;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; DENSITY FUNCTIONAL THEORY; HYDROLYSIS; PKA; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS; X RAY ANALYSIS;

EID: 53849145033     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja805686u     Document Type: Article

References (14)

1. (a) Meerwein, H. Org. Synth. 1966, 46, 113.
2. (b) Curphey, T. J. Org. Synth. 1971, 51, 142.
3. Olah, G. A.; Olah, J. A.; Svoboda, J. J. Synthesis 1973, 490.
4. Helmkamp, G. K.; Pettitt, D. J Org. Synth. 1966, 46, 122.
5. Meerwein, H.; Wunderlich, K. Angew. Chem. 1957, 69, 481.
6. The calculated NICS(1) values are 5, -9.64; 6, -11.73; benzene, -10.22 ppm. Since 5 and 6 are nonplanar, the NICS(1) shifts are artificially high. Planarization of 5 and 6 gives values of -11.45 and -14.09 ppm, respectively, and the actual shifts probably lie between the planar and nonplanar values. See: Mascal, M. J. Org. Chem. 2007, 72, 4323.
7. Thies, R. W.; Gasic, M.; Whalen, D.; Grutzner, J. B.; Sakai, M.; Johnson, B.; Winstein, S. J. Am. Chem. Soc. 1972, 94, 2262.
8. Lork, E.; Gortler, B.; Knapp, C.; Mews, R. Solid State Sci. 2002, 4, 1403.
9. Calculation performed using the Gaussian 03 program with default optimization parameters: Frisch, M. J.; et al. Gaussian 03, revision D.01; Gaussian, Inc.: Wallingford CT, 2004.
10. Woodward, R. B.; Fukanaga, T.; Kelly, R. C. J. Am. Chem. Soc. 1964, 86, 3162.
11. Compound 17 bears a close resemblance to a molecule synthesized over a decade ago by Prinzbach and co-workers. (Person, G.; Keller, M.; Prinzbach, H. Liebigs Ann. 1996, 507.
12. s symmetry on the NMR time scale and thus could be considered a time-averaged oxatriquinacenium species. The synthesis of oxatriquinanes from this or related precursors in these papers does not appear to have been further investigated.
13. Hext, N. M.; Hansen, J.; Blake, A. J.; Hibbs, D. E.; Hursthouse, M. B.; Shishkin, O. V.; Mascal, M. J. Org. Chem. 1998, 63, 6016.
14. Olah, G. A.; Prakash, G. K. S.; Barzaghi, M.; Lammertsma, K.; Schleyer, P. v. R.; Pople, J. A. J. Am. Chem. Soc. 1986, 108, 1032.