Photochemical deuterium exchange of the m-methyl group of 3-methylbenzophenone and 3-methylacetophenone in acidic D2O

Organic Letters

Volumn 6, Issue 11, 2004, Pages 1797-1799

  Huck, Lawrence A ^a   Wan, Peter ^a  

^a UNIVERSITY OF VICTORIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

3 METHYLACETOPHENONE; 3 METHYLBENZOPHENONE; ACETOPHENONE DERIVATIVE; ACID; BENZOPHENONE; CARBONYL DERIVATIVE; DEUTERIUM; DEUTERIUM OXIDE; METHYL GROUP; ORGANIC SOLVENT; OXYGEN; UNCLASSIFIED DRUG;

ACIDITY; AQUEOUS SOLUTION; ARTICLE; CHEMICAL REACTION; ION EXCHANGE; PHOTOCHEMISTRY; PHOTOLYSIS; PROTON TRANSPORT;

EID: 2942629611     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0494616     Document Type: Article

References (21)

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3. See for example: (a) Turro, N. J. Modern Molecular Photochemistry; University Science Books: Mill Valley, CA, 1991. (b) Scaiano, J. C. J. Photochem. 1973/74, 2, 81. (c) Garcia-Garibay, M. A.; Campos, L. M. In CRC Handbook of Organic Photochemistry and Photobiology, 2nd ed.; Horspool, W. M., Lenci, F., Eds.; CRC Press: Boca Raton, FL, 2004; Chapter 48. (d) Wagner, P. J.; Klán, P. In CRC Handbook of Organic Photochemistry and Photobiology, 2nd ed.; Horspool, W. M., Lenci, F., Eds.; CRC Press: Boca Raton, FL, 2004; Chapter 52. (e) Zimmerman, H. E.; Schuster, D. I. J. Am. Chem. Soc. 1962, 84, 4527.
4. See for example: (a) Turro, N. J. Modern Molecular Photochemistry; University Science Books: Mill Valley, CA, 1991. (b) Scaiano, J. C. J. Photochem. 1973/74, 2, 81. (c) Garcia-Garibay, M. A.; Campos, L. M. In CRC Handbook of Organic Photochemistry and Photobiology, 2nd ed.; Horspool, W. M., Lenci, F., Eds.; CRC Press: Boca Raton, FL, 2004; Chapter 48. (d) Wagner, P. J.; Klán, P. In CRC Handbook of Organic Photochemistry and Photobiology, 2nd ed.; Horspool, W. M., Lenci, F., Eds.; CRC Press: Boca Raton, FL, 2004; Chapter 52. (e) Zimmerman, H. E.; Schuster, D. I. J. Am. Chem. Soc. 1962, 84, 4527.
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17. 10 decayed with first-order kinetics, having a lifetime (τ) of 9000 ns at pH 7, decreasing to τ = 200 ns at pH 1.
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20. One referee has argued that structure 6b could be a ground-state species, that is, with a long σ bond joining the meta radicals, to give a non-Kekulé-type benzene structure. This would lead to a similar structure for 7b, although the overall mechanism would not change.
21. The apparent charge-transfer character of these aromatic ketone triplets (in aqueous solution) requires further study.