Decomposition of 2-(1-hydroxybenzyl)thiamin. Ruling out stepwise cationic fragmentation

Organic Letters

Volumn 2, Issue 14, 2000, Pages 2035-2036

  Moore, Ian F ^a   Kluger, Ronald ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AZIDE; CATION; DRUG DERIVATIVE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; PROTON; PYRIMIDINE DERIVATIVE; THIAMINE;

ARTICLE; CHEMISTRY;

AZIDES; CATIONS; INDICATORS AND REAGENTS; PROTONS; PYRIMIDINES; THIAMINE;

EID: 0034644014     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol005927i     Document Type: Article

References (10)

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2. Kluger, R.; Lam, J. F.; Pezacki, J. P.; Yang, C.-M. J. Am. Chem. Soc. 1995, 117, 11383.
3. Kluger, R.; Moore, I. F. J. Am. Chem. Soc. In press.
4. Zoltewicz, J. A.; Kauffman, G. M. J. Am. Chem. Soc. 1977, 99, 3134.
5. 3).
6. Synthesized by reaction of N(1′)-methylthiamin and sodium sulfite (0.1 equiv) in the presence of sodium azide (2.5 equiv). We have estimated the minimum amount detectable by NMR to be 0.1 mg or <0.5% based on NMHBzT.
7. McClelland, R. A. Tetrahedron 1996, 52, 6823.
8. Richard, J. P.; Toteva, M. M.; Crugeiras, J. J. Am. Chem. Soc. 2000, 122, 1664.
9. Uray, G.; Celotto, C.; Ibovnik, A.; Zoltewicz, J. A. J. Org. Chem. 1989, 54, 3941.
10. Less, A.; Nendel, M.; Wilsey, S.; Houk, K. N. J. Am. Chem. Soc. 1999, 121, 4524 and references therein.