Regiochemistry of intramolecular photocycloaddition of 1,3-dioxin-4-ones tethered through the ketal carbon

Tetrahedron Letters

Volumn 38, Issue 50, 1997, Pages 8663-8666

  Muller, Cheryl L ^a   Bever, Jason R ^a   Dordel, Mark S ^a   Kitabwalla, Moiz M ^a   Reineke, Theresa M ^a   Sausker, Justin B ^a   Seehafer, Troy R ^a   Li, Yu ^b   Jasinski, Jerry P ^b  

^a UNIVERSITY OF WISCONSIN EAU CLAIRE   (United States)

^b KEENE STATE COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 DIOXANE DERIVATIVE; CYCLOALKANE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOTOCHEMISTRY; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 0030834779     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10381-1     Document Type: Article

References (15)

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2. Winkler, J. D.; Bowen, C. M.; Liotta, F. Chem. Rev. 1995, 95, 2003-2020. Kaneko, C.; Sato, M., Sakaki, J.-I.; Abe, Y. J. Heterocyclic Chem. 1990, 27, 25-30.
3. Winkler, J. D.; Bowen, C. M.; Liotta, F. Chem. Rev. 1995, 95, 2003-2020. Kaneko, C.; Sato, M., Sakaki, J.-I.; Abe, Y. J. Heterocyclic Chem. 1990, 27, 25-30.
4. Sato, M; Abe, Y.; Ohuchi, H.; Kaneko, C. Heterocycles 1990, 31, 2115-2119.
5. Bihlmayer, G. A.; Derflinger, G.; Derkosch, J.; Polansky, O. E.; Monatsh. Chem. 1967, 98, 564-578.
6. Sato, M.; Sekiguchi, K.; Ogasawara, H.; Kaneko, C. Synthesis 1985, 224-226.
7. Henegar, K.E.; Winkler, J. D. Tetrahedron Lett. 1987, 1051-1054. Winkler, J. D.; Henegar, K. E.; Hong, B.-C.; Willard, P. G. J. Amer. Chem. Soc. 1994, 116, 4183-4188.
8. Henegar, K.E.; Winkler, J. D. Tetrahedron Lett. 1987, 1051-1054. Winkler, J. D.; Henegar, K. E.; Hong, B.-C.; Willard, P. G. J. Amer. Chem. Soc. 1994, 116, 4183-4188.
9. Sato M.; Abe, Y.; Takayama, K.; Sekiguchi, K.; Kaneko, C. J. Heterocyclic Chem. 1991, 28, 241-252.
10. The dioxinones were irradiated in a Rayonet reactor, 300 nm mercury lamps, Pyrex filter, at 3 to 15 mmolar concentration, in 1:9 acetone/acetonitrile.
11. b Lists of fractional atomic coordinates, displacement parameters, bond lengths and angles, and structure factor tables have been deposited at the Cambridge Crystallographic Data Center, U. K. as supplementary material, (a) Gilmore, C. J.; MITHRIL-An Integrated Direct Methods Computer Program. J. Appl. Cryst. 17, 42-46, Univ. of Glasgow, Scotland (1984)
12. (b) TEXSAN-TEXRAY Structure Analysis Package, Molecular Structure Corporation (1985).
13. (c) ORTEP. Johnson, C. K.; ORTEPII. Report ORNL-5138. Oak Ridge national Laboratory, Oak Ridge, TN (1976).
14. The crude samples contained traces of materials which may be the head to head isomers.
15. The esters 24 are separable on silica gel flash chromatography.