Preparation of Unsymmetrically Labeled Hydroperoxides. a Hydroxamate Ester-Nitrosation Approach

Journal of Organic Chemistry

Volumn 63, Issue 16, 1998, Pages 5547-5554

  Porter, Ned A ^a   Caldwell, Sarah E ^a   Lowe, Jennifer R ^a  

^a DUKE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001606529     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980654e     Document Type: Article

References (40)

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7. We have attempted, without success, to separate such hydroperoxide mixtures by pH controlled reverse-phase HPLC, S. E. Caldwell, Duke University Thesis, 1995. For reports of Chromatographic separation of isotopically labeled benzoic acids, see: (a) Tanaka, N.; Araki, M. J. Am. Chem. Soc. 1985,107, 7780. (b) Tanaka, N.; Yamaguchi, A.; Araki, M. J. Am. Chem. Soc. 1985, 107, 7781. (c) Tanaka, N.; Araki, M. J. Chromatogr. 1986, 352, 307.
8. We have attempted, without success, to separate such hydroperoxide mixtures by pH controlled reverse-phase HPLC, S. E. Caldwell, Duke University Thesis, 1995. For reports of Chromatographic separation of isotopically labeled benzoic acids, see: (a) Tanaka, N.; Araki, M. J. Am. Chem. Soc. 1985,107, 7780. (b) Tanaka, N.; Yamaguchi, A.; Araki, M. J. Am. Chem. Soc. 1985, 107, 7781. (c) Tanaka, N.; Araki, M. J. Chromatogr. 1986, 352, 307.
9. We have attempted, without success, to separate such hydroperoxide mixtures by pH controlled reverse-phase HPLC, S. E. Caldwell, Duke University Thesis, 1995. For reports of Chromatographic separation of isotopically labeled benzoic acids, see: (a) Tanaka, N.; Araki, M. J. Am. Chem. Soc. 1985,107, 7780. (b) Tanaka, N.; Yamaguchi, A.; Araki, M. J. Am. Chem. Soc. 1985, 107, 7781. (c) Tanaka, N.; Araki, M. J. Chromatogr. 1986, 352, 307.
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12. After our first report of the preparation of an unsymmetrically substituted hydroperoxide, see ref 7, a report appeared of the use of HOF to convert tert-butyl alcohol to tert-butyl hydroperoxide. HOF is reactive with a number of organic functional groups and would likely not be useful as a general reagent for the preparation of hydroperoxides, Zang, Y.; Kim, J.; Dong, Y. H.; Wilkinson E. C.; Appelman, E. H.; Que, L. J. Am. Chem. Soc. 1997, 119, 4197.
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31. The implicated peroxylactone, shown below, has been shown to be involved in chemiluminesence. See: (a) Sawaki, Y.; Ogata, Y. J. Org. Chem. 1977, 42, 40. (b) Adam, W.; del Fierro, J. J. Org. Chem. 1978, 43, 1159. Furthermore, nucleophiles react with the peroxylactone at the terminal oxygen rather than at the carbonyl carbon. See: Adam, W.; Blancafort, L. J. Org. Chem. 1997, 62, 1623. equation presented
32. The implicated peroxylactone, shown below, has been shown to be involved in chemiluminesence. See: (a) Sawaki, Y.; Ogata, Y. J. Org. Chem. 1977, 42, 40. (b) Adam, W.; del Fierro, J. J. Org. Chem. 1978, 43, 1159. Furthermore, nucleophiles react with the peroxylactone at the terminal oxygen rather than at the carbonyl carbon. See: Adam, W.; Blancafort, L. J. Org. Chem. 1997, 62, 1623. equation presented
33. The implicated peroxylactone, shown below, has been shown to be involved in chemiluminesence. See: (a) Sawaki, Y.; Ogata, Y. J. Org. Chem. 1977, 42, 40. (b) Adam, W.; del Fierro, J. J. Org. Chem. 1978, 43, 1159. Furthermore, nucleophiles react with the peroxylactone at the terminal oxygen rather than at the carbonyl carbon. See: Adam, W.; Blancafort, L. J. Org. Chem. 1997, 62, 1623. equation presented
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40. For the preparation of labeled benzoic acid see, Ponticorvo, L.; Rittenberg, D. J. Am. Chem. Soc. 1954, 76, 1705.