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a) J. R. Falck, D. K. Barma, R. Baati, C. Mioskowski, Angew. Chem. 2001, 113, 1321; Angew. Chem. Int. Ed. 2001, 40, 1281;
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Falck, J.R.1
Barma, D.K.2
Baati, R.3
Mioskowski, C.4
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2
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0035794912
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a) J. R. Falck, D. K. Barma, R. Baati, C. Mioskowski, Angew. Chem. 2001, 113, 1321; Angew. Chem. Int. Ed. 2001, 40, 1281;
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b) D. K. Barma, A. Kundu, H. M. Zhang, C. Mioskowski, J. R. Falck, J. Am. Chem. Soc. 2003, 125, 3218.
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J. Am. Chem. Soc.
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Barma, D.K.1
Kundu, A.2
Zhang, H.M.3
Mioskowski, C.4
Falck, J.R.5
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6
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0000727672
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M. Bandini, P. G. Cozzi, A. Umani-Ronchi, Angew. Chem. 2000, 112, 2417; Angew. Chem. Int. Ed. 2000, 39, 2327.
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Bandini, M.1
Cozzi, P.G.2
Umani-Ronchi, A.3
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7
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0034600784
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M. Bandini, P. G. Cozzi, A. Umani-Ronchi, Angew. Chem. 2000, 112, 2417; Angew. Chem. Int. Ed. 2000, 39, 2327.
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8
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0141741260
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2,2,2-Trichloroethyl esters undergo rearrangement to 1-halovinyl esters through a radical pathway known as a Surzur-Tanner rearrangement with a mixture of CuCl and bipyridine (1:1). See: R. N. Ram, N. K. Meher, Org. Lett. 2003, 5, 145.
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Org. Lett.
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Ram, R.N.1
Meher, N.K.2
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12
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0003412412
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Wiley, New York
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1-Chloroethyl benzoate probably arises through halide scrambling, see: M. B. Smith, J. March, March's Advanced Organic Chemistry : Reactions, Mechanisms, and Structure, 5th ed., Wiley, New York, 2001.
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(2001)
March's Advanced Organic Chemistry : Reactions, Mechanisms, and Structure, 5th Ed.
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Smith, M.B.1
March, J.2
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13
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16844368495
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1H NMR spectroscopy. The stereochemistry of 2e could not be determined by spectroscopy, but by analogy with the other compounds it is assumed that (Z)-2e is obtained.
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15
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16844364047
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note
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1H nOe NMR spectroscopy.
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18
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7444255993
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c) J. Mulzer, A. R. Strecker, L. Kattner, Tetrahedron Lett. 2004, 45, 8867.
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Tetrahedron Lett.
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Mulzer, J.1
Strecker, A.R.2
Kattner, L.3
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19
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33845471004
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The organochromium species undergo a rehybridization by placing a positive charge in a p orbital to produce a tight ion pair: a) H. M. Walborsky, M. Duraisamy, J. Am. Chem. Soc. 1984, 106, 5035; b) H. M. Walborsky, J. Rachon, V. Goedken, J. Am. Chem. Soc. 1986, 108, 7435.
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J. Am. Chem. Soc.
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Walborsky, H.M.1
Duraisamy, M.2
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20
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33845376318
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The organochromium species undergo a rehybridization by placing a positive charge in a p orbital to produce a tight ion pair: a) H. M. Walborsky, M. Duraisamy, J. Am. Chem. Soc. 1984, 106, 5035; b) H. M. Walborsky, J. Rachon, V. Goedken, J. Am. Chem. Soc. 1986, 108, 7435.
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J. Am. Chem. Soc.
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Walborsky, H.M.1
Rachon, J.2
Goedken, V.3
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21
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0000697108
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For a review on this and related reactions, see: A. L. J. Beckwith, D. Crich, P. J. Duggan, Q. Yao, Chem. Rev. 1997, 97, 3273.
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Chem. Rev.
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Beckwith, A.L.J.1
Crich, D.2
Duggan, P.J.3
Yao, Q.4
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22
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0001455738
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2X. However, this mechanism is unlikely as the formation of 2f (Table 1, entry 7) would require rearrangement to a quaternary center. For a review of the dyotropic rearrangement, see: M. T. Reetz, Tetrahedron 1973, 29, 2189.
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Tetrahedron
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Reetz, M.T.1
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23
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0001271448
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For an example of a postulated chromium(III)-carbene complex, see: M. H. Voges, C. Romming, M. Tilset, Organometallics 1999, 18, 529.
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Organometallics
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Voges, M.H.1
Romming, C.2
Tilset, M.3
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24
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0035913734
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R. Baati, D. K. Barma, J. R. Falck, C. Mioskowski, J. Am. Chem. Soc. 2001, 123, 9196.
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J. Am. Chem. Soc.
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Baati, R.1
Barma, D.K.2
Falck, J.R.3
Mioskowski, C.4
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25
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0000096360
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2O. See: a) P. L. Creger, J. Am. Chem. Soc. 1970, 92, 1396; b) D. Seebach, M. Boes, R. Naef, W. B. Schweizer, J. Am. Chem. Soc. 1983, 105, 5390.
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J. Am. Chem. Soc.
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Creger, P.L.1
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26
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33845551868
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2O. See: a) P. L. Creger, J. Am. Chem. Soc. 1970, 92, 1396; b) D. Seebach, M. Boes, R. Naef, W. B. Schweizer, J. Am. Chem. Soc. 1983, 105, 5390.
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J. Am. Chem. Soc.
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Seebach, D.1
Boes, M.2
Naef, R.3
Schweizer, W.B.4
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27
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16844371030
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note
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The fragmentation of β-sulfonate- and β-phosphate-substituted alkyl radicals is known to compete with the Surzur-Tanner rearrangement. See ref. [13].
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28
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0026752426
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The starting 2-alkoxy-substituted 1,1,1-trihaloalkanes were prepared according to: a) E. J. Corey, J. O. Link, Y. Shao, Tetrahedron Lett. 1992, 33, 3435; b) J. Russell, N. Roques, Tetrahedron 1998, 54, 13771; c) M. Shimizu, N. Yamada, Y. Takebe, T. Hata, M. Kuroboshi, T. Tamejiro Hiyama, Bull. Chem. Soc. Jpn. 1998, 71, 2903.
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Tetrahedron Lett.
, vol.33
, pp. 3435
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Corey, E.J.1
Link, J.O.2
Shao, Y.3
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29
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0032487852
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The starting 2-alkoxy-substituted 1,1,1-trihaloalkanes were prepared according to: a) E. J. Corey, J. O. Link, Y. Shao, Tetrahedron Lett. 1992, 33, 3435; b) J. Russell, N. Roques, Tetrahedron 1998, 54, 13771; c) M. Shimizu, N. Yamada, Y. Takebe, T. Hata, M. Kuroboshi, T. Tamejiro Hiyama, Bull. Chem. Soc. Jpn. 1998, 71, 2903.
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(1998)
Tetrahedron
, vol.54
, pp. 13771
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Russell, J.1
Roques, N.2
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30
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0032442654
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The starting 2-alkoxy-substituted 1,1,1-trihaloalkanes were prepared according to: a) E. J. Corey, J. O. Link, Y. Shao, Tetrahedron Lett. 1992, 33, 3435; b) J. Russell, N. Roques, Tetrahedron 1998, 54, 13771; c) M. Shimizu, N. Yamada, Y. Takebe, T. Hata, M. Kuroboshi, T. Tamejiro Hiyama, Bull. Chem. Soc. Jpn. 1998, 71, 2903.
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(1998)
Bull. Chem. Soc. Jpn.
, vol.71
, pp. 2903
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Shimizu, M.1
Yamada, N.2
Takebe, Y.3
Hata, T.4
Kuroboshi, M.5
Tamejiro Hiyama, T.6
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