Generation of carbenes via the photosensitization of spirodiaziridines with ketones

Journal of Organic Chemistry

Volumn 61, Issue 5, 1996, Pages 1560-1561

  Post, Alan J ^a   Morrison, Harry ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0346923609     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951734a     Document Type: Article

References (14)

1. Organic Photochemistry. 111 Part 110: Mohammad, T.; Morrison, H. J. Am. Chem. Soc., in press.
2. Post, A. J.; Nwaukwa, S.; Morrison, H. J. Am. Chem. Soc. 1994, 116, 6439-6440.
3. Post, A. J.; Morrison, H. J. Am. Chem. Soc. 1995, 117, 7812-7813
4. All photolyses were carried out using a Rayonet Reactor (New England Ultraviolet Co.) equipped with a rotating turntable. The reactor was fitted with 16 254 or 300 nm lamps. Argon-degassed solutions were irradiated in quartz (254 nm) or Pyrex (300 nm) photolysis tubes.
5. Turro, N. J. Modern Molecular Photochemistry; University Science Books. Mill Valler, CA, 1991; pp 380-381.
6. For reviews, see: (a) Baron, W. J.; DeCamp, M. R.; Hendrick, M. E.; Jones, J., Jr.; Levin, R. H.; Sohn, M. B. In Carbenes; Moss, R. A., Jones. J., Jr., Eds.; Wiley. New York, 1973; Vol. 1. (b) Kirmse, W. Carbene Chemistry; Academic Press: New York, 1968.
7. For reviews, see: (a) Baron, W. J.; DeCamp, M. R.; Hendrick, M. E.; Jones, J., Jr.; Levin, R. H.; Sohn, M. B. In Carbenes; Moss, R. A., Jones. J., Jr., Eds.; Wiley. New York, 1973; Vol. 1. (b) Kirmse, W. Carbene Chemistry; Academic Press: New York, 1968.
8. Freeman, P. K.; George, D. E.; Rao, V. N. M. J. Org. Chem. 1964, 29, 1682-1684.
9. Specific deuteration at C2 was readily determined by the absence of the characteristic proton resonance in the NMR spectrum.
10. Morgan, S.; Jackson, J. E.; Platz, M. S. J. Am. Chem. Soc. 1991, 113, 2782-2783 and references therein.
11. For a review, see: Cohen, S. G.; Parola, A., Parsons, G. H., Jr. Chem. Rev. 1973, 73, 141-161.
12. 13 one can determine that electron transfer should be appreciably more favorable to the p-dicyanobenzene. Both potential mechanisms discussed within the text ultimately invoke hydrogen abstraction by the sensitizer to create 7, either by homolytic or heterolytic pathways; the failure of the cyanoaromatic may lie in its relative inability to carry out this step.
13. Meites, L.; Zuman, P. CRC Handbook Series in Organic Electrochemistry; CRC Press: Cleveland, OH, 1976; Vol. I, pp 314, 338.
14. Murov, S. L. Handbook of Photochemistry; Marcel Dekker, Inc.: New York, 1973; pp 8, 11.