First stable and persistent 1,3-bisketene and trisketene

Journal of the American Chemical Society

Volumn 118, Issue 11, 1996, Pages 2768-2769

  Sung, Kuangsen ^a   Tidwell, Thomas T ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

KETENE DERIVATIVE;

ARTICLE; DRUG STABILITY; DRUG STRUCTURE; NUCLEAR MAGNETIC RESONANCE; ULTRAVIOLET SPECTROPHOTOMETRY;

EID: 0029917570     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9539554     Document Type: Article

References (24)

1. (a) Staudinger, H.; Kreis, W. Helv. Chim. Acta 1923, 6, 321-326.
2. (b) Diels, O., Wolf, B. Chem. Ber. 1906, 39, 689-697.
3. (c) McDonald, R. N.; Moms, D. L.; Petty, H. K.; Hoskins, T. L J. Chem. Soc., Chem. Commun. 1971, 743-744.
4. (d) Dixon, D. A.; Arduengo, A. J., III; Dobbs, K. D.; Khasnis, D. V. Tetrahedron Lett 1995, 36, 645-648.
5. (e) Maier, G.; Reisenauer, H. P.; Schafer, U.; Balli, H. Angew. Chem., Int. Ed. Engl. 1988, 27, 566-568
6. (f) Maier, G.; Reisenauer, H. P.; Ulrich, A. Tetrahedron Lett. 1991, 32, 4469-4472.
7. (a) Tidwell, T. T. Ketenes, Wiley, New York, 1995.
8. (b) Allen, A. D.; Ma. J., McAllister, M. A.; Tidwell, T. T.; Zhao, D.-c. Acc. Chem. Res. 1995, 28, 265-271.
9. (c) Allen, A. D.; Colomvakos, J. D.; Egle, I.; Lusztyk, J.; McAllister, M. A ; Tidwell, T T.; Wagner, B D., Zhao, D.-c. J. Am. Chem. Soc 1995, 117, 7552-7553.
10. (d) McAllister, M. A.; Tidwell, T. T. J. Am. Chem Soc. 1994, 116, 7233-7238.
11. (e) Zhao, D -c.; Allen, A. D.; Tidwell, T. T. J. Am Chem. Soc: 1993, 115, 10097-10103
12. (f) Allen, A. D : Ma, J.; McAllister, M. A.; Zhao, D-C. J. Chem. Soc., Perkin Trans. 2 1995, 847-851
13. 2, 140.0293; found, 140.0300.
14. (a) Allen, A. D.; Egle, I.; Janoschek, R.; Liu. H. W.; Ma, J.; Marra, R. M.; Tidwell, T. T. Chem. Lett., in press,
15. (b) Petukhov, V. A.; Zhun', V. I.; Sheludyakov, V. D.; Mironov, V. F. Zh, Obshch. Khim. 1979, 49, 1054-1057.
16. (c) Reed, A. E., Schade, C.; Schleyer, P. v. R.; Kamath, P. V.; Chandrasekhar, J. J. Chem. Soc., Chem. Commun. 1988, 67-69.
17. (d) Dallaire, C.; Brook, M. A.; Bain, A. D., Frampton, C. S.; Britten, J. F. Can. J. Chem. 1993, 71, 1676-1683.
18. (e) Luke, B. T.; Pople, J. A.; Krogh-Jespersen, M.-B., Apeloig, Y.; Chandrasekhar, J.; Schleyer, P. v. R. J. Am. Chem. Soc. 1986, 108, 260-269.
19. (f) Janes, N.; Oldfield, E. J. Am. Chem. Soc. 1986, 108, 5743-5753.
20. 3-Si 150.9851; found, 150.9843.
21. Frisch, M. J.; Trucks, G. W.; Head-Gordon. M.; Gill, P. M W.; Wong, M. W.; Foresman, J. B.; Johnson, B. G.; Schlegel, H. B.; Robb, M. A.; Replogle, E. S.; Gomperts, R.; Andres, J. L.; Raghavachari, K.; Binkley, J. S.; Gonzalez, C.; Martin, R. L.; Fox, D. J.; Defrees, D. J.; Baker, J.; Stewart, J. J. P.; Pople, J. A. Gaussian 92, Revision C; Gaussian Inc.: Pittsburgh. PA, 1992.
22. 2 of -592.3494, -742.9294, -441.7706, -291.1950, -330.2137, and -369.2330 hartees, respectively.
23. 2O] -298 (r = 0.998).
24. 4Si, 177 0583: found, 177.0593.