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1
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Kluger R. Chem. Rev. 90 (1990) 1151-1169
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Chem. Rev.
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Kluger, R.1
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3
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0004182589
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Schellenberger A., and Schowe R.L. (Eds), CRC, Boca Raton, FL
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In: Schellenberger A., and Schowe R.L. (Eds). Thiamine Pyrophosphate Biochemistry Vol. 1 (1988), CRC, Boca Raton, FL
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(1988)
Thiamine Pyrophosphate Biochemistry
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11
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0010469543
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Bisswanger H., and Ulrich J. (Eds), VCH, Weinheim
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Gotz F., and Sedewitz B. In: Bisswanger H., and Ulrich J. (Eds). Biochemistry and Physiology of Thiamine Diphosphate Enzymes (1991), VCH, Weinheim 286-293
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Biochemistry and Physiology of Thiamine Diphosphate Enzymes
, pp. 286-293
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Gotz, F.1
Sedewitz, B.2
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19
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0027416660
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and references therein
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Ferreira L.M., Chaves H.T., Lobo A.M., Prabhakar S., and Rzepa H.S. J. Chem. Soc., Chem. Commun. (1993) 133-134 and references therein
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J. Chem. Soc., Chem. Commun.
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Ferreira, L.M.1
Chaves, H.T.2
Lobo, A.M.3
Prabhakar, S.4
Rzepa, H.S.5
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20
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0022001065
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Both O-acyl arylhydroxylamines and N-arylhydroxamic acids are implicated in carcinogenesis, see:
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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
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(1985)
Carcinogenesis
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, pp. 251-258
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Flammang, T.J.1
Westra, J.G.2
Kadlubar, F.F.3
Beland, F.A.4
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23
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11544291121
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Compound 16d prepared by adoption of the procedure described for (-)-menthyl 2,2′-diphenylcyclopropanecarboxylate:
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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
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(1959)
J. Am. Chem. Soc.
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, pp. 1514-1515
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Impastato, F.J.1
Barash, L.2
Walborsky, H.M.3
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27
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0025155821
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Barletta G.A., Chung C., Rios C.B., Jordan F., and Schlegel J.M. J. Am. Chem. Soc. 112 (1990) 8144-8149
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(1990)
J. Am. Chem. Soc.
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, pp. 8144-8149
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Barletta, G.A.1
Chung, C.2
Rios, C.B.3
Jordan, F.4
Schlegel, J.M.5
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29
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0028500492
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For detection of phenylhydronitroxide, formed probably by an H atom abstraction from NADHP and ascorbic acid by PhNO, see:
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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
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(1994)
Free Radic. Res.
, vol.21
, pp. 235-243
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Fujii, H.1
Koscielniak, J.2
Kakinuma, K.3
Berliner, L.J.4
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31
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46349102160
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note
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5 (see Section 4).
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33
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46349100473
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note
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2, with NaH as the base, gave PhNHOAc, PhN(OH)Ac, azoxybenzene and aniline in 20, 18, 8 and 25% yields, respectively.
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34
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46249134253
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note
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2.
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36
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0000327515
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The ring opening tendency of diphenylcyclopropyl methyl radical is reported to be an order of magnitude greater than that of the unsubstituted one:
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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
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(1992)
J. Am. Chem. Soc.
, vol.114
, pp. 10915-10921
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Newcomb, M.1
Johnson, C.C.2
Manek, M.B.3
Varick, T.R.4
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37
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46349109365
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note
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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.
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38
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46349109521
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note
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3N.
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39
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33845470407
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+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:
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+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
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(1984)
J. Am. Chem. Soc.
, vol.106
, pp. 3374-3376
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Semmelhack, M.F.1
Schmid, C.R.2
Cortes, D.A.3
Chou, C.S.4
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41
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46349094012
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note
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2O addition.
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44
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0033554021
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TEMPO is reported to oxidise 9,10-dihydroanthracene and 1,4-cyclohexadiene to the corresponding aromatic compounds:
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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
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(1999)
J. Am. Chem. Soc.
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, pp. 6375-6381
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Ciriano, M.V.1
Korth, H.G.2
Scheppingen, W.B.3
Mulder, P.4
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45
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46349090043
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note
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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).
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46
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0001400078
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For the detection and identification of phenylhydronitroxide from PhNO and PhNHOH under neutral conditions, see:
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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
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(1967)
J. Am. Chem. Soc.
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, pp. 3821-3828
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Russell, G.A.1
Geels, E.J.2
Smentows, F.J.3
Chang, K.Y.4
Reynolds, J.5
Kaupp, G.6
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49
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37049081038
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For a detailed discussion on azoxybenzene formation from PhNHOH and PhNO, see:
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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
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(1990)
J. Chem. Soc., Perkin Trans. 2
, pp. 759-764
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Pizzolatti, M.G.1
Yunes, R.A.2
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50
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46349087340
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note
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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.
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51
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0010885258
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A kinetic isotope effect of 4-6 is typical of a primary isotope effect for proton transfers from carbon acids to hydroxide ion, see:
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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
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(1993)
J. Am. Chem. Soc.
, vol.115
, pp. 14-20
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Casamassina, T.E.1
Huskey, W.P.2
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55
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46349087883
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note
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5 was purchased from Aldrich Chemical Co. Ltd, Gillingham, Dorset, UK.
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61
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0001742548
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Novak M., Pelecanou M., Roy A.K., Andronico A.F., Plourde F.M., Olefirowicz T.M., and Curtin T.J. J. Am. Chem. Soc. 106 (1984) 5623-5631
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(1984)
J. Am. Chem. Soc.
, vol.106
, pp. 5623-5631
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Novak, M.1
Pelecanou, M.2
Roy, A.K.3
Andronico, A.F.4
Plourde, F.M.5
Olefirowicz, T.M.6
Curtin, T.J.7
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