Cycloaddition reactions of sodium dinitroxytrioxide (Angeli's salt)

Tetrahedron Letters

Volumn 40, Issue 29, 1999, Pages 5279-5282

  Torun, Lokman ^a   Mohammad, Taj ^a   Morrison, Harry ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 NAPHTHALDEHYDE; 1 NAPHTHOIC ACID; 1,3 DIPHENYLISOBENZOFURAN; ALDEHYDE; CARBOXYLIC ACID; HYDROXAMIC ACID; ISOBENZOFURAN DERIVATIVE; METHANOL; NAPHTHALENE DERIVATIVE; SODIUM DERIVATIVE; SODIUM TRIOXODINITRATE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CHEMICAL REACTION; HYDROLYSIS; REACTION ANALYSIS;

EID: 0033575421     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00962-4     Document Type: Article

References (10)

1. (a) Angeli, A. Gazz. Chim. Ital. 1903, 33, 245; (b) Angeli, A. Ahrens Samm. Chem. Tech. Vorträge 1908, 13, 2.
2. (a) Angeli, A. Gazz. Chim. Ital. 1903, 33, 245; (b) Angeli, A. Ahrens Samm. Chem. Tech. Vorträge 1908, 13, 2.
3. Smith, P. A. S.; Hein, G. H. J. Am. Chem. Soc. 1960, 82, 5731.
4. 3; cf. Veprek-Siska, J.; Simirous, F.; Pliska, V. Collect. Czech. Chem. Commun. 1959, 24, 1175.
5. Donald, C. E.; Hughes, M. N.; Thompson, J. M.; Bonner, F. T. Inorg. Chem. 1986, 25, 2676.
6. Merkel, P. B.; Kearns, D. R. J. Am. Chem. Soc. 1975, 97, 462.
7. Bonner, F. T.; Akhtar, M. J. Inorg. Chem. 1981, 20, 3155.
8. Akasaka, T.; Nakagawa, M.; Ando, W. J. Org. Chem. 1986, 51, 4477. We find the formation of this product to be markedly accelerated by light. It would appear that the reaction involves the DPIBF photosensitized formation of singlet oxygen and the subsequent reaction of the DPIBF ground state with this species.
9. Cheronis, N. D.; Entrikin, J. B. Semimicro Qualitative Organic Analysis; Thomas Y. Crowell Co.: New York, 1947; p. 123.
10. The alcohol reduction product is observed at longer reaction times. This is the apparent co-product (with the carboxylic acid) of a Cannizaro reaction; control studies show the Cannizaro to be minor side-reaction at both room and reflux temperatures during the typical (<2 h) reaction times.