X-Ray and MO analysis of highly stereoselective solid-state photocycloadditions of 2-pyrones with maleimide

Tetrahedron

Volumn 58, Issue 30, 2002, Pages 6111-6116

  Shimo, Tetsuro ^a   Uezono, Takahiro ^a   Obata, Toru ^a   Yasutake, Mikio ^b   Shinmyozu, Teruo ^b   Somekawa, Kenichi ^a  

^a KAGOSHIMA UNIVERSITY   (Japan)

^b KYUSHU UNIVERSITY   (Japan)

Author keywords

2 pyrones; Cycloaddition; Hydrogen bonding; Solid state photochemistry; Transition state analysis

Indexed keywords

2 PYRONE DERIVATIVE; 4 (2 BIPHENYLMETHYLOXY) 6 METHYL 2 PYRONE; 4 (4 CHLOROBENZYLOXY) 6 METHYL 2 PYRONE; 4 (9 ANTHRYLMETHYLOXY) 6 METHYL 2 PYRONE; 6 METHYL 4 (2 METHYLBENZYLOXY) 2 PYRONE; 6 METHYL 4 (3 METHYLBENZYLOXY) 2 PYRONE; 6 METHYL 4 DIPHENYLMETHYLOXY 2 PYRONE; 7 METHYL 11 METHYLBENZYLOXY 8 OXA 4 AZATRICYCLO[5.4.0.0 2,6]UNDEC 10 EN 3,5,9 TRIONE; BENZYL DERIVATIVE; MALEIMIDE; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; CHEMICAL INTERACTION; CRYSTAL STRUCTURE; CYCLOADDITION; HYDROGEN BOND; IRRADIATION; PHOTOREACTIVITY; PRIORITY JOURNAL; QUANTITATIVE ANALYSIS; REACTION ANALYSIS; SOLID; STEREOCHEMISTRY; X RAY DIFFRACTION;

EID: 0037157797     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)00582-3     Document Type: Article

References (14)

1. Ito Y. Synthesis. 1998;1-32. and references cited therein.
2. Ito Y., Fujita H. Chem. Lett. 2000;288-289.
3. Tanaka K., Toda F. Chem. Rev. 100:2000;1025-1074. and references cited therein.
4. Koshima H., Matsushige D., Miyauchi M., Fujita J. Tetrahedron. 56:2000;6845-6852.
5. Obata T., Shimo T., Yoshimoto S., Somekawa K., Kawaminami M. Chem. Lett. 1999;181-182.
6. Obata T., Shimo T., Yasutake M., Shinmyozu T., Kawaminami M., Yoshida R., Somekawa K. Tetrahedron. 57:2001;1531-1541.
7. Shimo T., Yano H., Yasutake M., Shinmyozu T., Somekawa K. Anal. Sci. 2002;. in press.
8. Pauling L. The Nature of the Chemical Bonds. 1960;Cornell University, Ithaca, NY. p 260.
9. (a) Dewar M.J.S., Jie C., Yu J. Tetrahedron. 49:1993;5003-5038.
10. (b) Dado D., Gellman S.H. J. Am. Chem. Soc. 114:1992;3138-3139.
11. Shimo T., Yasutake M., Shinmyozu T., Somekawa K. Anal. Sci. 18:2002;613-614.
12. Cox P.J., Parker S.F. Acta Crystallogr. C52:1996;2578-2580.
13. Gilmore, C. J. MITHRIL: An Integrated Direct Methods Computer Program; University of Glasgow, Scotland, 1990.
14. Crystal Structure Analysis Package; Molecular Structure Corporation, 1985 and 1999.