The aza-type-B photochemical rearrangement: The role of a second carbonyl in heterocyclic photochemistry. Mechanistic and exploratory organic photochemistry

Journal of Organic Chemistry

Volumn 72, Issue 16, 2007, Pages 6091-6096

  Zimmerman, Howard E ^a   Mitkin, Oleg D ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; CARBONYLATION; CYCLOHEXANE; SUBSTITUTION REACTIONS;

CARBONYL GROUP; CHEMICAL EQUATION; HETEROCYCLIC PHOTOCHEMISTRY; ORGANIC PHOTOCHEMISTRY;

PHOTOCHEMICAL REACTIONS;

ARTICLE; CONJUGATION; PHOTOCHEMISTRY; PHOTOLYSIS; REACTION ANALYSIS; SYNTHESIS;

EID: 34547629264     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0706372     Document Type: Article

References (14)

1. This is Paper 283 of our general series.
2. (a) For Paper 282, see: Zimmerman, H. E. Pure Appl. Chem. 2006, 2193-2203.
3. Porter Award Address. (b) For Paper 281, see: Zimmerman, H. E.; Mitkin, O. J. Am. Chem. Soc. 2006, 128, 12743-12749.
4. (a) Zimmerman, H. E.; Wilson, J. W. J. Am. Chem. Soc. 1964, 86, 4036-4042.
5. (b) Zimmerman, H. E.; Rieke, R. D.; Scheffer, J. R. J. Am. Chem. Soc. 1967, 89, 2033-2047.
6. (c) Zimmerman, H. E.; Hancock, K. G. J. Am. Chem. Soc. 1968, 90, 3749-3760.
7. Reich, H. J. Org. Synth. 1980, 59, 58-65.
8. Urech, E.; Tagmann, E.; Sury, E.; Hoffmann, K. Helv. Chim. Acta 1953, 36, 1809-1815.
9. Bretschneider, H.; Deutscher, H.; Klotzer, W.; Sander, M. Monatsh. Chem. 1958, 89, 288-300.
10. Izzo, P. T. J. Org. Chem. 1963, 28, 1713-1715.
11. Gill, G. B.; James, G. D.; Oates, K. V.; Pattenden, G. J. Chem. Soc., Perkin Trans. 1 1993, 21, 2567-2580.
12. (a) Baltzly, R.; Mehta, N. B.; Russell, P. B.; Brooks, R. E.; Grivsky, E. M.; Steinberg, A. M. J. Org. Chem. 1962, 27, 213-218.
13. (b) The bicyclic-[3.1.0] photoproduct, geminally substituted with two substituents originally at C-4, is structurally parallel to the type-A photoproducts of 2,5-cyclohexadienones. However, mechanistically, these arise from an oxa-di-π-methane rearrangement as subsequently noted.
14. The diffractometry was performed by Dr. Ilia Guzei, and we gratefully acknowledge helpful advice from Dr. Ilia Guzei on our Shelxtl computations.