Wavelength-dependent photochemistry of diazo Meldrum's acid and its spirocyclic isomer, diazirino Meldrum's acid: Wolff rearrangement versus isomerization

Journal of the American Chemical Society

Volumn 125, Issue 6, 2003, Pages 1456-1457

  Bogdanova, Aneta ^a   Popik, Vladimir V ^a  

^a BOWLING GREEN STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACID; DIAZIRINO MELDRUMS ACID; DIAZOMELDRUMS ACID; SPIRO COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DECOMPOSITION; ISOMER; ISOMERISM; MOLECULAR DYNAMICS; PHOTOCHEMISTRY; PHOTOLYSIS; PHOTOREACTIVITY; REACTION ANALYSIS; WOLFF REARRANGEMENT;

AZO COMPOUNDS; DIAZOMETHANE; DIOXANES; ISOMERISM; PHOTOCHEMISTRY; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 0037433268     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja029528p     Document Type: Article

References (21)

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9. Preparation of compounds 1, 2, and 3 is presented in the Supporting Information.
10. Bogdanova, A.; Popik V. V. Manuscript in preparation.
11. The results of DFT calculations are presented in the Supporting Information.
12. Photo-Wolff reaction of 1 in solution and polymer matrices has been reported before: Lippert, T.; Koskelo, A.; Stoutland, P. O. J. Am. Chem. Soc. 1996, 118, 1551; Fujiwara, H.; Nakajima, Y.; Fukumura, H.; Masuhara, H. J. Phys. Chem. 1995, 99, 11481; Winnik, M. A.; Wang, F.; Nivaggioli, T.; Hruska, Z.; Fukumura, H.; Masuhara, H. J. Am. Chem. Soc. 1991, 113, 9702; Stevens, R. V.; Bisacchi, G. S.; Goldsmith, L.; Strouse, C. E. J. Org. Chem. 1980, 45, 2708; Kammula, S. L.; Tracer, H. L.; Shelvin, P. B.; Jones, M., Jr. J. Org. Chem. 1977, 42, 2931.
13. Photo-Wolff reaction of 1 in solution and polymer matrices has been reported before: Lippert, T.; Koskelo, A.; Stoutland, P. O. J. Am. Chem. Soc. 1996, 118, 1551; Fujiwara, H.; Nakajima, Y.; Fukumura, H.; Masuhara, H. J. Phys. Chem. 1995, 99, 11481; Winnik, M. A.; Wang, F.; Nivaggioli, T.; Hruska, Z.; Fukumura, H.; Masuhara, H. J. Am. Chem. Soc. 1991, 113, 9702; Stevens, R. V.; Bisacchi, G. S.; Goldsmith, L.; Strouse, C. E. J. Org. Chem. 1980, 45, 2708; Kammula, S. L.; Tracer, H. L.; Shelvin, P. B.; Jones, M., Jr. J. Org. Chem. 1977, 42, 2931.
14. Photo-Wolff reaction of 1 in solution and polymer matrices has been reported before: Lippert, T.; Koskelo, A.; Stoutland, P. O. J. Am. Chem. Soc. 1996, 118, 1551; Fujiwara, H.; Nakajima, Y.; Fukumura, H.; Masuhara, H. J. Phys. Chem. 1995, 99, 11481; Winnik, M. A.; Wang, F.; Nivaggioli, T.; Hruska, Z.; Fukumura, H.; Masuhara, H. J. Am. Chem. Soc. 1991, 113, 9702; Stevens, R. V.; Bisacchi, G. S.; Goldsmith, L.; Strouse, C. E. J. Org. Chem. 1980, 45, 2708; Kammula, S. L.; Tracer, H. L.; Shelvin, P. B.; Jones, M., Jr. J. Org. Chem. 1977, 42, 2931.
15. Photo-Wolff reaction of 1 in solution and polymer matrices has been reported before: Lippert, T.; Koskelo, A.; Stoutland, P. O. J. Am. Chem. Soc. 1996, 118, 1551; Fujiwara, H.; Nakajima, Y.; Fukumura, H.; Masuhara, H. J. Phys. Chem. 1995, 99, 11481; Winnik, M. A.; Wang, F.; Nivaggioli, T.; Hruska, Z.; Fukumura, H.; Masuhara, H. J. Am. Chem. Soc. 1991, 113, 9702; Stevens, R. V.; Bisacchi, G. S.; Goldsmith, L.; Strouse, C. E. J. Org. Chem. 1980, 45, 2708; Kammula, S. L.; Tracer, H. L.; Shelvin, P. B.; Jones, M., Jr. J. Org. Chem. 1977, 42, 2931.
16. Photo-Wolff reaction of 1 in solution and polymer matrices has been reported before: Lippert, T.; Koskelo, A.; Stoutland, P. O. J. Am. Chem. Soc. 1996, 118, 1551; Fujiwara, H.; Nakajima, Y.; Fukumura, H.; Masuhara, H. J. Phys. Chem. 1995, 99, 11481; Winnik, M. A.; Wang, F.; Nivaggioli, T.; Hruska, Z.; Fukumura, H.; Masuhara, H. J. Am. Chem. Soc. 1991, 113, 9702; Stevens, R. V.; Bisacchi, G. S.; Goldsmith, L.; Strouse, C. E. J. Org. Chem. 1980, 45, 2708; Kammula, S. L.; Tracer, H. L.; Shelvin, P. B.; Jones, M., Jr. J. Org. Chem. 1977, 42, 2931.
17. Formation of small amounts of diazirine 2 in photolysis of 1 was reported previously: Nikolaev, V. A.; Khimich, N. N.; Korobitsyna, I. K. Khim. Geterotsikl Soedin. 1985, 321; Livinghouse, T.; Stevens, R. V. J. Am. Chem. Soc. 1978, 100, 6479.
18. Formation of small amounts of diazirine 2 in photolysis of 1 was reported previously: Nikolaev, V. A.; Khimich, N. N.; Korobitsyna, I. K. Khim. Geterotsikl Soedin. 1985, 321; Livinghouse, T.; Stevens, R. V. J. Am. Chem. Soc. 1978, 100, 6479.
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21. Wang, J.-L.; Toscano, J. P.; Platz, M. S.; Nikolaev, V.; Popik, V. J. Am. Chem. Soc. 1995, 117, 5477.