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0000793596
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Publication no. 56 in a series on alkane diazonium ion-pairs and deamination. Preceding publication: White, E. H. et al. J. Org. Chem. 1996, 61, 7986.
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(a) White, E. H.; Field, K. W.; Hendrickson, W. H.; Dzadzic, P.; Roswell, D. F.; Paik, S.; Mullen, P. W. J. Am. Chem. Soc. 1992, 114, 8023.
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Hendrickson, W.H.3
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Paik, S.6
Mullen, P.W.7
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Roswell, D.F.5
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4
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0001654884
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(c) White, E. H.; McGirk, R. H.; Aufdermarsh, C. A.; Jr.; Tiwari, H. P.; Todd, M. J. J. Am. Chem. Soc. 1973, 95, 8107.
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White, E.H.1
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Aufdermarsh Jr., C.A.3
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(d) White, E. H.; Tiwari, H. P.; Todd, M. J. J. Am. Chem. Soc. 1968, 90, 4734.
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White, E.H.1
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Todd, M.J.3
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7
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85086526325
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4b
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4b
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8
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85086528168
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note
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2b,4b
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9
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0004043430
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Patai, S., Ed.; John Wiley and Sons, Inc.: New York; Chapter 8
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(a) White, E. H.; Woodcock, D. J. In The Chemistry of the Amino Group; Patai, S., Ed.; John Wiley and Sons, Inc.: New York, 1968; Chapter 8.
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The Chemistry of the Amino Group
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White, E.H.1
Woodcock, D.J.2
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10
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1542707029
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Ph.D. Thesis of Ron W. Darbeau, The Johns Hopkins University, Baltimore, Maryland
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(b) From the Ph.D. Thesis of Ron W. Darbeau, The Johns Hopkins University, Baltimore, Maryland, 1996.
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(1996)
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11
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85086526409
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note
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4b
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14
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0011664156
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(a) White, E. H.; Ribi, M. A.; Cho, L. K.; Egger, N.; Dzadzic, P. M.; Todd, M. D. J. Org. Chem. 1984, 49, 4866.
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White, E.H.1
Ribi, M.A.2
Cho, L.K.3
Egger, N.4
Dzadzic, P.M.5
Todd, M.D.6
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16
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0006385393
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(c) White, E. H.; Maskill, H.; Woodcock, D. J.; Schroeder, M. A. Tetrahedron Lett. 1969, 1713.
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Tetrahedron Lett.
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White, E.H.1
Maskill, H.2
Woodcock, D.J.3
Schroeder, M.A.4
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17
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0344189878
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(d) White, E. H.; Lewis, C. P.; Ribi, M. A.; Ryan, T. J. J. Org. Chem. 1981, 46, 552.
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White, E.H.1
Lewis, C.P.2
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Ryan, T.J.4
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19
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0005166731
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(f) Olah, G. A.; Friedman, N.; Bollinger, J. M.; Lukas, J. J. Am. Chem. Soc. 1966, 88, 5328.
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Olah, G.A.1
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21
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0003491446
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Muller, E., Ed., (Houben-Weyl), Georg Thieme Verlag: Stuttgart
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(h) Soll, H. Methoden der Organischen Chemie; Muller, E., Ed., (Houben-Weyl), Georg Thieme Verlag: Stuttgart, 1958; Vol. 11, Part 2, p 133.
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Soll, H.1
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0004061168
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Chapman and Hall: London
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(a) Joule, J. A.; Mills, K.; Smith, G. F. Heterocyclic Chemistry, 3rd ed., Chapman and Hall: London, 1995; pp 231-232.
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Joule, J.A.1
Mills, K.2
Smith, G.F.3
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24
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1542497337
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(c) N-Alkylpyrroles, however, are readily prepared by reaction of pyrryl salts with iodoalkanes (Candy, C. F.; Jones, A. R. J. Org. Chem. 1971, 36, 3990 and Hobbs, C. F. et al. J. Am. Chem. Soc., 1962, 84, 43).
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J. Org. Chem.
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Candy, C.F.1
Jones, A.R.2
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25
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33947474732
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(c) N-Alkylpyrroles, however, are readily prepared by reaction of pyrryl salts with iodoalkanes (Candy, C. F.; Jones, A. R. J. Org. Chem. 1971, 36, 3990 and Hobbs, C. F. et al. J. Am. Chem. Soc., 1962, 84, 43).
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J. Am. Chem. Soc.
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Hobbs, C.F.1
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26
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1542602026
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Half-lives were determined by measuring the changes in the integral of the benzyl signal as a function of time at a constant temperature in the NMR probe
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(a) Half-lives were determined by measuring the changes in the integral of the benzyl signal as a function of time at a constant temperature in the NMR probe.
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27
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85086528304
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note
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4b benzylation would be faster.
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28
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85086527405
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note
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1H NMR or GC and by GC, respectively (see ref 2e for comparison).
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30
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0344898021
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8b and 6.4 (Friedrich, E. C.; Vartanian, P. F. J. Organomet. Chem. 1976, 110, 159). Since oxygen is more electronegative than nitrogen it would be expected to deshield the benzylic protons to a greater extent than would nitrogen (Silverstein, R. M.; Bassler, G. C.; Morrill, T. C. Spectrometric Identification of Organic Compounds, 4th ed.; John Wiley and Sons: New York, 1981; p 220).
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J. Organomet. Chem.
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Friedrich, E.C.1
Vartanian, P.F.2
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31
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0003520774
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John Wiley and Sons: New York
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8b and 6.4 (Friedrich, E. C.; Vartanian, P. F. J. Organomet. Chem. 1976, 110, 159). Since oxygen is more electronegative than nitrogen it would be expected to deshield the benzylic protons to a greater extent than would nitrogen (Silverstein, R. M.; Bassler, G. C.; Morrill, T. C. Spectrometric Identification of Organic Compounds, 4th ed.; John Wiley and Sons: New York, 1981; p 220).
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Spectrometric Identification of Organic Compounds, 4th Ed.
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Silverstein, R.M.1
Bassler, G.C.2
Morrill, T.C.3
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32
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85086527233
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note
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4a,13
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34
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1542707035
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note
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(a) Ideal data would be obtained by decomposing the same precursor (e.g., 1a) at the same temperature in a medium comprised of the solvent under study dissolved in a large excess (∼90%) of an inert diluent.
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35
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85086526446
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2c
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2c
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36
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1542602017
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McManus, S. P.; Ed., Academic Press: New York
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(a) McManus, S. P.; Pittman, C. U., Jr. Organic Reactive Intermediates; McManus, S. P.; Ed., Academic Press: New York, 1973; Vol. 26, p 299.
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McManus, S.P.1
Pittman Jr., C.U.2
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0001064551
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(b) McClelland, R. A.; Banait, N.; Steenken, S. J. Am. Chem. Soc. 1986, 108, 7023.
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McClelland, R.A.1
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Steenken, S.3
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85086527622
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4b
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4b
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41
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1542392460
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note
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4e Thus it would appear that phenyldiazomethane on general acid protonation leads directly to the corresponding intimate ion-pair and eventually into the nitrogen-separated ion-pair (eqs 1 and 4) which is the active alkylating agent in these deaminations. Ion-pair formation is likely to be facilitated in more polar solvents such as acetone and methanol.
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44
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0017341720
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(a) Lee, K.; Gold, B.; Mirvish, S. Mutat. Res. 1977, 48, 131.
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Lee, K.1
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45
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0002624810
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Chemical Carcinogenesis
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Searle, C., Ed., ACS Monograph No. 182, American Chemical Society, Washington, DC
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(b) Preussman, R.; Stewart, B. W. Chemical Carcinogenesis; Searle, C., Ed., ACS Monograph No. 182, American Chemical Society, Washington, DC, 1984; pp 643-828.
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Preussman, R.1
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48
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(c) Groves, J. K.; Anderson, H. J.; Nagy, H. Can. J. Chem. 1971, 49, 2427.
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Groves, J.K.1
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Katritzky, A. R.; Lang, H.; Lan, X. Tetrahedron 1993, 49, 2829.
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Katritzky, A.R.1
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0011912744
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Pelter, A.; Rowlands, M.; Clements, G. Synthesis 1987, (1), 51.
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Pelter, A.1
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