Crystal lattice photochemistry often proceeds in discrete stages. Mechanistic and exploratory organic photochemistry

Organic Letters

Volumn 2, Issue 8, 2000, Pages 1169-1170

  Zimmerman, Howard E ^a   Nesterov, Evgueni E ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001603194     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0057838     Document Type: Article

References (14)

1. This is Paper 255 of our general series.
2. For Paper 254 see Zimmerman, H. E.; Alabugin, I. V. J. Am. Chem. Soc. 2000, 121, 952-953.
3. (a) Hitherto, there have been literature examples where a reaction has been described as proceeding with continuous product variation.
4. (b) For example, note Teng, M.; Lauber, J. W.; Fowler F. W. J. Org. Chem. 1991, 56, 6840-6845.
5. Zimmerman, H. E.; Alabugin, I. V.; Chen, W.-C, Zhu, Z. J. Am. Chem. Soc. 1999, 121, 11930-11931.
6. (a) Zimmerman, H. E.; Wilson, J. W. J. Am. Chem. Soc. 1964, 86, 4036-4042.
7. (b) Zimmerman, H. E.; Hancock, K. G. J. Am. Chem. Soc. 1968, 90, 3749-3760.
8. (c) For a review, see: Schuster, D. I. In Rearrangements in Ground and Excited States; P. DeMayo, Ed.; Academic Press: New York, 1980; Vol. 3.
9. Zimmerman, H. E.; St. Clair, J. D. J. Org. Chem. 1989, 54, 2125-2137.
10. (a) Zimmerman, H. E.; Zhu, Z., J. Am. Chem. Soc. 1995, 117, 5245-5262.
11. (b) It is clear that this did not result from melting as evidenced by monitoring the crystal shape and melting point throughout the photolysis. The minimum melting point was 80°C while the run was at 0°C.
12. 1 were found, and only the latter, that described here, was found to be reactive.
13. This is derived in the Supporting Information.
14. Regime 2 is more complex than in the first two examples in that cis - trans isomerization of the product of stage 1 occurs. This does not affect the interpretation.