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Volumn 19, Issue 17, 2009, Pages 4971-4973

Use of comparative triazolinium triflate fragmentation rates as a tool to assay relative competency of Brønsted bases in N→N proton transfer

Author keywords

Additive effects; Ammonium triflate; Fragmentation; Heterocycle; Olefin aminohydroxylation

Indexed keywords

2,4 OXAZOLIDINEDIONE DERIVATIVE; ALCOHOL; AZIDE; BENZYL DERIVATIVE; BRONSTED BASE; ETHER; IMIDE; N,N DIMETHYLFORMAMIDE; TRIAZOLINE DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID; WATER;

EID: 68349158659     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.07.067     Document Type: Article
Times cited : (5)

References (24)
  • 2
    • 37849005442 scopus 로고    scopus 로고
    • Carbon to oxygen proton transfer in triosephosphate isomerase (TIM):
    • Carbon to oxygen proton transfer in triosephosphate isomerase (TIM):. O'Donoghue A.C., Amyes T.L., and Richard J.P. Org. Biomol. Chem. 6 (2008) 391
    • (2008) Org. Biomol. Chem. , vol.6 , pp. 391
    • O'Donoghue, A.C.1    Amyes, T.L.2    Richard, J.P.3
  • 6
    • 34548724094 scopus 로고    scopus 로고
    • Carbonic anhydrase, lead reference:
    • Carbonic anhydrase, lead reference:. Silverman D.N., and McKenna R. Acc. Chem. Res. 40 (2007) 669
    • (2007) Acc. Chem. Res. , vol.40 , pp. 669
    • Silverman, D.N.1    McKenna, R.2
  • 11
    • 0000614865 scopus 로고
    • For theoretical and experimental treatments of acid-catalyzed 1-alkyl triazolines, see:
    • For theoretical and experimental treatments of acid-catalyzed 1-alkyl triazolines, see:. Wladkowski B.D., Smith R.H., and Michejda C.J. J. Am. Chem. Soc. 113 (1991) 7893
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 7893
    • Wladkowski, B.D.1    Smith, R.H.2    Michejda, C.J.3
  • 15
  • 21
    • 68349129612 scopus 로고    scopus 로고
    • note
    • The experimental protocol for Table 1 employed 200 mol % TfOH (instead of 100 mol %), as we have previously demonstrated that this merely slows the fragmentation to a measurable level, but does not otherwise affect reaction outcome. See Ref. 9 for details.
  • 24
    • 68349136335 scopus 로고    scopus 로고
    • note
    • +-OTf spectroscopically, but this may be due to its own demethylation by amine added at reaction quench, or demethylation by acetonitrile upon warming to ambient temperature.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.