메뉴 건너뛰기




Volumn 64, Issue 33, 2008, Pages 7759-7770

Reaction of aromatic nitroso compounds with chemical models of 'thiamine active aldehyde'

Author keywords

[No Author keywords available]

Indexed keywords

3,4 DIMETHYLTHIAZOLIUM TRIFLUOROMETHANESULFONATE; ALDEHYDE; AROMATIC COMPOUND; CYCLOPROPANE DERIVATIVE; HETEROCYCLIC COMPOUND; NITROSO DERIVATIVE; NITROXIDE DERIVATIVE; PHENYLHYDRONITROXIDE; THIAMINE; THIAZOLE DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID;

EID: 46349100846     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.06.008     Document Type: Article
Times cited : (8)

References (68)
  • 1
  • 3
    • 0004182589 scopus 로고
    • Schellenberger A., and Schowe R.L. (Eds), CRC, Boca Raton, FL
    • In: Schellenberger A., and Schowe R.L. (Eds). Thiamine Pyrophosphate Biochemistry Vol. 1 (1988), CRC, Boca Raton, FL
    • (1988) Thiamine Pyrophosphate Biochemistry , vol.1
  • 20
    • 0022001065 scopus 로고
    • Both O-acyl arylhydroxylamines and N-arylhydroxamic acids are implicated in carcinogenesis, see:
    • Both O-acyl arylhydroxylamines and N-arylhydroxamic acids are implicated in carcinogenesis, see:. Flammang T.J., Westra J.G., Kadlubar F.F., and Beland F.A. Carcinogenesis 6 (1985) 251-258
    • (1985) Carcinogenesis , vol.6 , pp. 251-258
    • Flammang, T.J.1    Westra, J.G.2    Kadlubar, F.F.3    Beland, F.A.4
  • 23
    • 11544291121 scopus 로고
    • Compound 16d prepared by adoption of the procedure described for (-)-menthyl 2,2′-diphenylcyclopropanecarboxylate:
    • Compound 16d prepared by adoption of the procedure described for (-)-menthyl 2,2′-diphenylcyclopropanecarboxylate:. Impastato F.J., Barash L., and Walborsky H.M. J. Am. Chem. Soc. 81 (1959) 1514-1515
    • (1959) J. Am. Chem. Soc. , vol.81 , pp. 1514-1515
    • Impastato, F.J.1    Barash, L.2    Walborsky, H.M.3
  • 29
    • 0028500492 scopus 로고
    • For detection of phenylhydronitroxide, formed probably by an H atom abstraction from NADHP and ascorbic acid by PhNO, see:
    • For detection of phenylhydronitroxide, formed probably by an H atom abstraction from NADHP and ascorbic acid by PhNO, see:. Fujii H., Koscielniak J., Kakinuma K., and Berliner L.J. Free Radic. Res. 21 (1994) 235-243
    • (1994) Free Radic. Res. , vol.21 , pp. 235-243
    • Fujii, H.1    Koscielniak, J.2    Kakinuma, K.3    Berliner, L.J.4
  • 31
    • 46349102160 scopus 로고    scopus 로고
    • note
    • 5 (see Section 4).
  • 33
    • 46349100473 scopus 로고    scopus 로고
    • note
    • 2, with NaH as the base, gave PhNHOAc, PhN(OH)Ac, azoxybenzene and aniline in 20, 18, 8 and 25% yields, respectively.
  • 34
    • 46249134253 scopus 로고    scopus 로고
    • note
    • 2.
  • 36
    • 0000327515 scopus 로고
    • The ring opening tendency of diphenylcyclopropyl methyl radical is reported to be an order of magnitude greater than that of the unsubstituted one:
    • The ring opening tendency of diphenylcyclopropyl methyl radical is reported to be an order of magnitude greater than that of the unsubstituted one:. Newcomb M., Johnson C.C., Manek M.B., and Varick T.R. J. Am. Chem. Soc. 114 (1992) 10915-10921
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 10915-10921
    • Newcomb, M.1    Johnson, C.C.2    Manek, M.B.3    Varick, T.R.4
  • 37
    • 46349109365 scopus 로고    scopus 로고
    • note
    • It is tacitly assumed that the rearranged radical once formed would pick up a H atom or an electron from any reducing species existing in the reaction mixture rather than re-close.
  • 38
    • 46349109521 scopus 로고    scopus 로고
    • note
    • 3N.
  • 39
    • 33845470407 scopus 로고
    • +1 is known to oxidise benzylic, primary and secondary alcohols. The failure of benzhydrol or benzyl alcohol to undergo any oxidation under the conditions mentioned (5 equiv, TEMPO) showed that the 2-acetylthiazolium salt was not formed due to the adventitious presence of such transition metals in the solvent used:
    • +1 is known to oxidise benzylic, primary and secondary alcohols. The failure of benzhydrol or benzyl alcohol to undergo any oxidation under the conditions mentioned (5 equiv, TEMPO) showed that the 2-acetylthiazolium salt was not formed due to the adventitious presence of such transition metals in the solvent used:. Semmelhack M.F., Schmid C.R., Cortes D.A., and Chou C.S. J. Am. Chem. Soc. 106 (1984) 3374-3376
    • (1984) J. Am. Chem. Soc. , vol.106 , pp. 3374-3376
    • Semmelhack, M.F.1    Schmid, C.R.2    Cortes, D.A.3    Chou, C.S.4
  • 41
    • 46349094012 scopus 로고    scopus 로고
    • note
    • 2O addition.
  • 44
    • 0033554021 scopus 로고    scopus 로고
    • TEMPO is reported to oxidise 9,10-dihydroanthracene and 1,4-cyclohexadiene to the corresponding aromatic compounds:
    • TEMPO is reported to oxidise 9,10-dihydroanthracene and 1,4-cyclohexadiene to the corresponding aromatic compounds:. Ciriano M.V., Korth H.G., Scheppingen W.B., and Mulder P. J. Am. Chem. Soc. 121 (1999) 6375-6381
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 6375-6381
    • Ciriano, M.V.1    Korth, H.G.2    Scheppingen, W.B.3    Mulder, P.4
  • 45
    • 46349090043 scopus 로고    scopus 로고
    • note
    • In this context it is interesting to note that in reactions of pyruvate oxidoreductases the radical derived from a one-electron transfer to thiamine diphosphate may be a universal intermediate because these enzymes typically carry one-electron oxidations mediated by iron-sulfur centres (see Ref. 1d, p 11 and references therein).
  • 46
    • 0001400078 scopus 로고
    • For the detection and identification of phenylhydronitroxide from PhNO and PhNHOH under neutral conditions, see:
    • For the detection and identification of phenylhydronitroxide from PhNO and PhNHOH under neutral conditions, see:. Russell G.A., Geels E.J., Smentows F.J., Chang K.Y., Reynolds J., and Kaupp G. J. Am. Chem. Soc. 89 (1967) 3821-3828
    • (1967) J. Am. Chem. Soc. , vol.89 , pp. 3821-3828
    • Russell, G.A.1    Geels, E.J.2    Smentows, F.J.3    Chang, K.Y.4    Reynolds, J.5    Kaupp, G.6
  • 49
    • 37049081038 scopus 로고
    • For a detailed discussion on azoxybenzene formation from PhNHOH and PhNO, see:
    • For a detailed discussion on azoxybenzene formation from PhNHOH and PhNO, see:. Pizzolatti M.G., and Yunes R.A. J. Chem. Soc., Perkin Trans. 2 (1990) 759-764
    • (1990) J. Chem. Soc., Perkin Trans. 2 , pp. 759-764
    • Pizzolatti, M.G.1    Yunes, R.A.2
  • 50
    • 46349087340 scopus 로고    scopus 로고
    • note
    • It should be noted that a close similarity exists between the reactions of ArNHOH and 2-acetylthiazolium salts on one hand, and that of ArNO and hydroxyethyl thiazolium salts on the other, in so far as the products are concerned. However, the fact that hydroxamic acid was never obtained with the former reagents strongly indicates that its formation does not involve isomerisation of ArNHOAc.
  • 51
    • 0010885258 scopus 로고
    • A kinetic isotope effect of 4-6 is typical of a primary isotope effect for proton transfers from carbon acids to hydroxide ion, see:
    • A kinetic isotope effect of 4-6 is typical of a primary isotope effect for proton transfers from carbon acids to hydroxide ion, see:. Casamassina T.E., and Huskey W.P. J. Am. Chem. Soc. 115 (1993) 14-20
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 14-20
    • Casamassina, T.E.1    Huskey, W.P.2
  • 55
    • 46349087883 scopus 로고    scopus 로고
    • note
    • 5 was purchased from Aldrich Chemical Co. Ltd, Gillingham, Dorset, UK.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.