Photochemistry of aryloxiranes: Free radical 1,2-alkyl migrations in a constrained system

Photochemical and Photobiological Sciences

Volumn 3, Issue 9, 2004, Pages 851-853

  Arney, Benny E ^a   White, Rick C ^a   Ramanathan, Ahalya ^a   Barham, Laura ^a   Sherrod, Stacy ^a   McCall, Paula ^a   Livanec, Philip ^a   Mangus, Kimberly ^a   White, Katherine ^a  

^a SAM HOUSTON STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ETHYLENE OXIDE DERIVATIVE; FLUORENE DERIVATIVE; FREE RADICAL;

ALKYLATION; ARTICLE; CHEMICAL BOND; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; OXIDATION REDUCTION REACTION; PHOTOCHEMISTRY; PHOTOLYSIS; PHOTOOXIDATION; PHOTOREACTIVITY; PRIORITY JOURNAL; REACTION TIME; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 7244229681     PISSN: 1474905X     EISSN: 14749092     Source Type: Journal    
DOI: 10.1039/b408341e     Document Type: Article

References (16)

1. R. S. Becker R. O. Bost J. Kolc N. Bertoniere R. Smith G. W. Griffin Spectroscopy and Photochemistry of Aryloxiranes J. Am. Chem. Soc. 1970 92 1302.
2. H. Kristinnson G. W. Griffin Photochemistry of Phenyloxiranes II., New Precursor for Phenyl Carbene J. Am. Chem. Soc. 1966 88 1579.
3. J. Brokatzky-Geiger W. Eberbach Thermal and Photochemical Studies with Stilbene Oxides: Intramolecular Trapping of Carbonyl Ylid Intermediates Tetrahedron Lett. 1984 25 1137.
4. H. Kristinnson G. W. Griffin Angew. Chem., Int. Ed. Engl. 1965 4 868.
5. S. Linder K. White M. Palmer B. E. Arney R. C. White Geometric Requirements for the Photolysis of Aryloxiranes and Cyclic Carbonate Esters Tetrahedron Lett. 2002 43 1169.
6. H. Kristinnson G. W. Griffin Photocyclization of 3,3-Dimethyl-1-phenylbutene-1. A Novel Photoinduced 1,2-Methyl Migration J. Am. Chem. Soc. 1966 88 378.
7. H. E. Zimmerman J. Heydinger Rearrangement of 1,3-Diradicals. Arylcyclopropane Photochemistry J. Org. Chem. 1991 56 1747.
8. D. Armesto M. J. Ortiz A. R. Agarrabeita Photochemical Vinylcyclopropane Rearrangements of 1-Substituted 3-(2,2-diphenylvinyl)-2,2-dimethylcyclopropanes to Cyclopropentenes and Different Heterocycles J. Org. Chem. 1999 64 1056.
9. H. E. Zimmerman A. P. Kamath Diradical Rearrangements: An Unusual 1,2-Shift in a Photochemically Generated 1,3-Diradical. Mechanistic and Exploratory Organic Photochemistry J. Am. Chem. Soc. 1988 110 900.
10. K. Mizuno H. Maeda H. Sugita S. Nishioka T. Hirai A. Sugimoto Photorearrangement of Vinylidenecyclopropanes to 1,2,3-Butatriene Derivatives Org. Lett. 2001 3 581.
11. R. C. White K. Lynch E. Wedyck Ring Contraction in the Photochemistry of 1,2-Dihydronaphthalene Oxide J. Photochem. Photobiol. A: Chem. 1993 71 127.
12. Epoxide 5 was made via MCPBA oxidation of 9-isopropylidene fluorene: A. Blazek M. Pungente E. Krogh P. Wan Photosolvolysis of 9-fluorenylderivatives in aqueous solution – exploratory studies of reactivity of photogenerated 9-fluorenyl cations J. Photochem. Photobiol. A: Chem. 1992 64 315.
13. P. C. Wong D. Griller J. C. Scaiano A Kinetic Study of the Reactions of Carbonyl Ylids Formed by the Addition of Fluorenylidene to Ketones J. Am. Chem. Soc. 1982 104 6631.
14. N. J. Bunce J. LaMarre S. P. Vaish Photorearrangement of Azoxybenzene to 2-Hydroxyazobenzene: A Convenient Chemical Actinometer Photochem. Photobiol. 1984 39 531.
15. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, Jr., R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. G. Johnson, W. Chen, M. W. Wong, J. L. Andres, M. Head-Gordon, E. S. Replogle and J. A. Pople, GAUSSIAN 98 (Revision A.6), Gaussian, Inc., Pittsburgh, PA, 1998.
16. T. Nakano K. Takewaki T. Yade Y. Okamoyo Dibenzofulvene, a 1,1-Diphenylethylene Analogue, Gives a π Stacked Polymer by Anionic, Free Radical and Cationic Catalysts J. Am. Chem. Soc. 2001 123 9182.