Crystallographic evidence for cyclopropane ring formation in isotwistenes obtained by thermal cascade reactions of cyclopentadienone with acyclic conjugated dienes

Chemical and Pharmaceutical Bulletin

Volumn 57, Issue 7, 2009, Pages 749-751

  Yamaguchi, Koki ^a   Eto, Masashi ^b   Yoshitake, Yasuyuki ^a   Harano, Kazunobu ^a  

^a SOJO UNIVERSITY   (Japan)

^b TOKAI UNIVERSITY   (Japan)

Author keywords

Cyclopentadienone; Cyclopropane ring; Density functional theory calculation; Double Diels Alder reaction; Pericyclic reaction; X ray analysis

Indexed keywords

CYCLOPENTADIENE DERIVATIVE; CYCLOPROPANE; MUCONALDEHYDE;

ARTICLE; CHEMICAL REACTION KINETICS; CRYSTAL STRUCTURE; DENSITY FUNCTIONAL THEORY; NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS; THERMODYNAMICS; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; CYCLOPENTANES; CYCLOPROPANES; MODELS, MOLECULAR; MOLECULAR STRUCTURE;

EID: 67650841806     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.57.749     Document Type: Article

References (22)

1. Harano K., Uchida K., Izuma M., Aoki T., Eto M., Hisano T., Chem. Pharm. Bull., 36, 2312-2322 (1988).
2. Harano K., Aoki T., Eto M., Hisano T., Chem. Pharm. Bull., 38, 1182-1191 (1990).
3. Eto M., Harano K. T., Hisano T., J. Chem. Soc. Perkin Trans. 2, 1993, 963-966 (1993).
4. Eto M., Aoki T., Harano K., Tetrahedron, 50, 13395-13408 (1994).
5. Jikyo T., Eto M., Harano K., Tetrahedron, 53, 12415-12424 (1997).
6. Jikyo T., Eto M., Harano T., Chem. Pharm. Bull., 45, 1961-1969 (1997).
7. Stewart J. J. P., J. Am. Chem. Soc., 107, 3902-3909 (1985).
8. Stewart J. J. P., J. Comput. Chem., 10, 209-220 (1989).
9. Stewart J. J. P., J. Comput. Chem., 10, 221-264 (1989).
10. WinMOPAC Ver. 3.9, Fujitsu Ltd., Tokyo, Japan, 1997-2004.
11. The heats of reaction are as follows: 14.7 kcal/mol (AM1); 8.1 kcal/mol (PM3); 5.1 kcal/mol (PM5); -3.8 kcal/mol (HF/6-31G*). The reaction barriers are as follows: 56.0 kcal/mol (AM1); 53.3 kcal/mol (PM3); 39.9 kcal/mol (PM5); 48.2 kcal/mol (HF/6-31G*).
12. Gaussian 03, Revision C.02, Frisch M. J., Trucks G. W., Schlegel H. B., Scuseria G. E., Robb M. A., Cheeseman J. R., Montgomery Jr. J. A., Vreven T., Kudin K. N., Burant J. C., Millam J. M., Iyengar S. S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G. A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J. E., Hratchian H. P., Cross J. B., Bakken V., Adamo C., Jaramillo J., Gomperts R., Stratmann R. E., Yazyev O., Austin A. J., Cammi R., Pomelli C., Ochterski J. W., Ayala P. Y., Morokuma K., Voth G. A., Salvador P., Dannenberg J. J., Zakrzewski V. G., Dapprich S., Daniels A. D., Strain M. C., Farkas O., Malick D. K., Rabuck A. D., Raghavachari K., Foresman J. B., Ortiz J. V., Cui Q., Baboul A. G., Clifford S., Cioslowski J., Stefanov B. B., Liu G., Liashenko A., Piskorz P., Komaromi I., 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., Gonzalez C., Pople J. A., Gaussian, Inc., Wallingford CT, 2004.
13. Johnson C. K., "ORTEP, Report ORNL-3794," Oak Ridge National Laboratory, Tennessee, U.S.A., 1965.
14. Hoffmann R., Tetrahedron Lett., 1970, 2907-2910 (1970).
15. Wong H. N. C., Hon M.-Y., Tse C.-W., Yip Y.-C., Tanko J., Hudlicky T., Chem. Rev., 89, 165-195 (1989).
16. Fukui K., "Kagaku Hanno to Densi no Kido (Chemical Reactions and Electron Orbitals)," Maruzen, Tokyo, 1976.
17. Fleming I., "Frontier Orbitals and Chemical Reactions," Wiley, London, 1976.
18. Sustmann R., Trill H., Angew. Chem., Int. Ed. Engl., 11, 838-840 (1972).
19. SIR92: Altomare A., Cascarano G., Giacovazzo C., Guagliardi A., Burla M., Polidori G., Camalli M., J. Appl. Cryst., 27, 435 (1994).
20. CrystalStructure 3.6.0: Crystal Structure Analysis Package, Rigaku and Rigaku/MSC, 9009 New Trails Dr. The Woodlands TX 77381 U.S.A., (2000-2004).
21. Watkin D. J., Prout C. K., Carruthers J. R., Betteridge P. W., "CRSTAL Issue 10," Chemical Crystallography Laboratory, Oxford, 1996.
22. Scott A. P., Radom L., J. Phys. Chem., 100, 10502-10513 (1996).