Regio- and stereoselective [2+2] photodimerization of 3-substituted 2-alkoxy-2-oxo-2H-1,2-benzoxaphosphorines

Molecules

Volumn 7, Issue 5, 2002, Pages 420-432

  Nikolova, Rositca D ^a   Vayssilov, G N ^a   Rodios, Nestor ^a   Bojilova, Anka ^a  

^a NONE

Author keywords

2 Oxo 2 alkoxy 1,2 benzoxaphosphorines; Benzoxaphphorine dimers; 2+2 photocycloaddition

Indexed keywords

DIMER; METHANOL; PHOSPHORUS DERIVATIVE;

ARTICLE; DIMERIZATION; EPIMER; EVAPORATION; STEREOCHEMISTRY; STEREOISOMERISM; SUBSTITUTION REACTION; SUNLIGHT;

EID: 3343011368     PISSN: 14203049     EISSN: None     Source Type: Journal    
DOI: 10.3390/70500420     Document Type: Article

References (30)

1. Darbarwar, M.; Sundaramurthy, V. Synthesis of Coumarins with 3:4-Fused Ring Systems and their Physiological Activity. Synthesis, 1982, 337.
2. Von Wesseley, F.; Plaichinger, I. Über die Konstitution der Photodimerisate der Coumarrine und Furocoumarine. Chem. Ber., 1942, 75, 971.
3. Mustafa, A.; Kamel, M.; Allam, M. A. Dimerization Reaction in Sunlight. V. Photodimerization of Substituted Coumarins. J. Org. Chem., 1957, 22, 888.
4. Schenck, G. O.; Wilucki, I.; Krauch, C. H. Photosensibilisierte Cyclodimerisation von Coumarin. Chem. Ber., 1962, 95, 1409.
5. Leenders, L. H.; Schouteden, E.; Schryver, F. C. D. Photochemistry of Nonconjucated Bichromophoric Systems. Cyclomerization of 7,7′- Polymethylenedioxycoumarins and Polymethylenedicarboxylic Acid (7-Coumarinyl) Diesters. J.Org.Chem., 1973, 38, 957.
6. Rao, D. V.; Ulrich, H.; Stuber, F. A.; Sayigh, A. A. R. Über die Photocyclodimerisation substituirter Cumarine. Chem. Ber., 1973, 106, 338.
7. Abdou, W. M.; Born, L.; Hulpke, H.; Mahran, M. R.; Sidky, M. M.; Wamhoff, H. Photochemistry of Pesticides, 7. Regioselective Photodimerization of o,o-Diethyl-o-(3-Chloro-4-Methylcoumarin-7-yl)-Thiophosphate (Coumaphos). Phosphorus and Sulphur, 1987, 29, 179.
8. Saigo, K.; Sekimoto, K.; Yonezawa, N.; Hasegawa, M. Optical Resolution of Anti Head-to-Head Coumarin Dimer and Determination of Absolute Configuration Based on CD Spectral Data. Tetrahedron Lett., 1983, 24, 5381.
9. Saigo, K.; Nakamura, M.; Adegawa, Y.; Noguchi, S.; Hasegawa, M. Preparation, Chiroptical properties, and Chiral Recognition Ability of Carbamoylated Polyamides Having (-)-Anti Head-to-Head Coumarin Dimer Component. Chem. Lett. Chem. Soc. Jpn., 1989, 337.
10. Yonesawa, M.; Kanoe, T.; Saigo, K.; Hasegawa, M. J. Polymer Science, 1993, 31, 667.
11. Mori, K.; Murai, O.; Hahimoto, S.; Nakamura, Y. Highly Regio- and Stereoselective Photocycloaddition between Coumarin and Thymine by Molecular Recognition. Tetrahedron Lett., 1996, 37, 8523.
12. Otsuki, T. Photochemical Reaction of Furocoumarin (Psoralen). The Reactive Site In Its Photo-excited State. Chem. Lett. Chem. Soc. Jpn., 1987, 453.
13. Ratiner, B. D.; Otsuki, T. Photochemical Reactivity of 3-Ethoxycarbonylfurocoumarin. Chem. Lett. Chem. Soc. Jpn., 1989, 1035.
14. Moghaddam, M. J.; Matsuda, T. Molecular Design of Three-Dimensional Artificial Extracellular Matrix: Photosensitive Polymers Containing Cell Adhesive Peptide. J. Polymer Science, 1993, 31, 1589.
15. Chen, Y.; Chen, K. H. Synthesis and Reversible Photocleavage of Novel Polyurethanes Containing Coumarin Dimer Compounds. J. Polymer Science, 1997, 35A, 613.
16. Chen, Y.; Chou, C. F. Reversible Photodimerization of Coumarin Derivatives Dispersed in Poly(vinylacetate). J. Polymer Science, 1995, 33A, 2705.
17. Hammond, G. S.; Stout, C. A.; Lamola, A. A. Mechanisms of Photochemical Reactions in Solution. XXV. The Photodimerization of Coumarin. J. Am. Chem. Soc., 1964, 86, 3103.
18. Morrison, H.; Curtis, H.; McDowell, T. Solvent Effects on The Photodimerization of Coumarin. J. Am. Chem .Soc., 1966, 88, 5415.
19. Muthuramu, K.; Ramamurthy, V. Photodimerization of Coumarin in Aqueous and Micellar Media. J. Org. Chem., 1982, 47, 3976.
20. Gnanaguru, K.; Ramasubbu, N.; Venkatesan, K.; Ramamurthy, V. A Study on the Photochemical Dimerization of Coumarin in the Solid State. J. Org. Chem., 1985, 50, 2337.
21. Krauch, C. H.; Farid, S.; Schenck, G. O. Photo-C4-Cyclodimerization von Coumarin. Chem. Ber., 1966, 99, 625.
22. Bojilova, A.; Nikolova, R.; Ivanov, C.; Rodios, N. A.; Terzis, A.; Raptopoulou, C. P. A comparative Study of the Interaction of Salicylaldehydes with Phosphonoacetates under Knoevenagel Reaction Conditions. Synthesis of 1,2-Benzoxaphosphorines and their Dimers. Tetrahedron, 1996, 52, 12597.
23. Kirpichonok, M. A.; Melnikova, L. M.; Yufit, D. S.; Struchkov, Y. T.; Grandberg, I.I.; Denisov, L. K. Khim. Heterocikl. Soed., 1988, 1176.
24. Kirpichonok, M. A.; Melnikova, L. M.; Denisov, L. K.; Grandberg, I.I. Khim. Heterocikl. Soed., 1988, 1169.
25. March, J. Advanced Organic Chemistry. John Wiley & Sons: New York, 1985; p. 753.
26. Hoffman, R.; Wells, P.; Morrison, H. Organic Photochemistry. XII. Further Studies on the Mechanism of Coumarin Photodimerization. Observation of an Unusual "Heavy Atom" Effect. J. Org. Chem., 1971, 36, 102.
27. Koziar, J. C.; Cowan, D. O. Photochemical Heavy-Atom Effects. Acc. Chem .Res., 1978, 11, 334.
28. Harrison, R. J.; Nichols, J. A.; Straatsma, T. P.; Dupuis, M.; Bylaska, E. J.; Fann, G. I.; Windus, T. L.; Apra, E.; Anchell, J.; Bernholdt, D.; Borowski, P.; Clark, T.; Clerc, D.; Dachsel, H.; de Jong, B.; Deegan, M.; Dyall, K.; Elwood, D.; Fruchtl, H.; Glendenning, E.; Gutowski, M.; Hess, A.; Jaffe, J.; Johnson, B.; Ju, J.; Kendall, R.; Kobayashi, R., Kutteh, R.; Lin, Z.; Littlefield, R.; Long, X.; Meng, B.; Nieplocha, J., Niu, S.; Rosing, M.; Sandrone, G.; Stave, M.; Taylor, H.; Thomas, G.; van Lenthe, J.; Wolinski, K.; Wong, A.; Zhang, Z. NWChem, A Computational Chemistry Package for Parallel Computers, Version 4.0″ (2000), Pacific Northwest National Laboratory, Richland, Washington 99352-0999, USA.
29. Becke, A. D. J. Chem Phys., 1993, 98, 5648.
30. Glendening, E. D.; Badenhoop, J. K.; Reed, A. E.; Carpenter, J. E.; Weinhold, F. NBO 4.M, Theoretical Chemistry Institute, University of Wisconsin, Madison, WI, 1999.