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f) H. J. Reich, S. Wollowitz, J. E. Trend, F. Chow, D. F. Wendelborn. ibid. 1978, 43, 1697;
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b) For recent enantioselective applications see: A. S. Gokhale, A. B. E. Minidis, A. Pfaltz, Tetrahedron Lett. 1995, 36, 1831; M. N. Andrus, A. B. Argade, X. Chen, M. G. Pamment, ibid. 1995, 36, 2945; C. Zondervan, B. L. Feringa, Tetrahedron Asymmetry 1996, 7, 1898; A. D. Gupta, V. K. Sing, Tetrahedron Lett. 1996, 37, 2633; M. J. Södergren, P. G. Andersson, ibid. 1996, 37, 7577.
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Gokhale, A.S.1
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0028931670
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b) For recent enantioselective applications see: A. S. Gokhale, A. B. E. Minidis, A. Pfaltz, Tetrahedron Lett. 1995, 36, 1831; M. N. Andrus, A. B. Argade, X. Chen, M. G. Pamment, ibid. 1995, 36, 2945; C. Zondervan, B. L. Feringa, Tetrahedron Asymmetry 1996, 7, 1898; A. D. Gupta, V. K. Sing, Tetrahedron Lett. 1996, 37, 2633; M. J. Södergren, P. G. Andersson, ibid. 1996, 37, 7577.
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14
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0028931670
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-
b) For recent enantioselective applications see: A. S. Gokhale, A. B. E. Minidis, A. Pfaltz, Tetrahedron Lett. 1995, 36, 1831; M. N. Andrus, A. B. Argade, X. Chen, M. G. Pamment, ibid. 1995, 36, 2945; C. Zondervan, B. L. Feringa, Tetrahedron Asymmetry 1996, 7, 1898; A. D. Gupta, V. K. Sing, Tetrahedron Lett. 1996, 37, 2633; M. J. Södergren, P. G. Andersson, ibid. 1996, 37, 7577.
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Zondervan, C.1
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15
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0029965482
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b) For recent enantioselective applications see: A. S. Gokhale, A. B. E. Minidis, A. Pfaltz, Tetrahedron Lett. 1995, 36, 1831; M. N. Andrus, A. B. Argade, X. Chen, M. G. Pamment, ibid. 1995, 36, 2945; C. Zondervan, B. L. Feringa, Tetrahedron Asymmetry 1996, 7, 1898; A. D. Gupta, V. K. Sing, Tetrahedron Lett. 1996, 37, 2633; M. J. Södergren, P. G. Andersson, ibid. 1996, 37, 7577.
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Gupta, A.D.1
Sing, V.K.2
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16
-
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0030583506
-
-
b) For recent enantioselective applications see: A. S. Gokhale, A. B. E. Minidis, A. Pfaltz, Tetrahedron Lett. 1995, 36, 1831; M. N. Andrus, A. B. Argade, X. Chen, M. G. Pamment, ibid. 1995, 36, 2945; C. Zondervan, B. L. Feringa, Tetrahedron Asymmetry 1996, 7, 1898; A. D. Gupta, V. K. Sing, Tetrahedron Lett. 1996, 37, 2633; M. J. Södergren, P. G. Andersson, ibid. 1996, 37, 7577.
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Södergren, M.J.1
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2642617965
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b) A. Heumann, B. Åkermark, Angew Chem. 1984, 96, 443; Angew. Chem. Int. Ed. Engl. 1984, 23, 453 ;
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b) A. Heumann, B. Åkermark, Angew Chem. 1984, 96, 443; Angew. Chem. Int. Ed. Engl. 1984, 23, 453 ;
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c) A. Heumann, B. Åkermark, S. Hansson, T. Rein, Organic Synthesis, Vol. 68, pp. 109;
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Heumann, A.1
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d) A. Heumann, M. Reglier, B. Waegell, Angew. Chem. 1982, 94, 397; Angew. Chem. Int. Ed. Engl. 1982, 18, 366;
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Principato, B.1
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S. Hansson, A. Heumann, T. Rein, B. Åkermark, J. Org. Chem. 1990, 55, 975.
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Hansson, S.1
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a) J. E. Bäckvall, R. B. Hopkins, H. Grennberg, M. M. Mader, A. K. Awasthi, J. Am. Chem. Soc. 1990, 112, 5160;
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Bäckvall, J.E.1
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b) S. E. Byström, E. M. Larsson, B. Å̊kermark, J. Org. Chem. 1990,55,5674;
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d) H. Grennberg, K. Bergstad, J. E. Bäckvall, J. Mol. Catal. A 1996, 113, 355;
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e) K. Bergstad, H. Grennberg. J. E. Bäckvall, Organometallics, 1998, 77, 45.
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C. Jia, P. Müller, H. Mimoun, J. Mol. Catal. A 1995, 707, 127.
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Jia, C.1
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32
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0001022539
-
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An extension to allow carboxylate nucleophiles other than acetate has further increased the utility of the reaction. See: B. Äkermark, E. M. Larsson, J. D. Oslob, J. Org. Chem. 1994, 59, 5729.
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J. Org. Chem.
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Äkermark, B.1
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34
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33747838053
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W. Kitching, Z. Rappoport, S. Winstein, W. G. Young, J. Am. Chem. Soc. 1966, 88, 2054.
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Kitching, W.1
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38
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37049107993
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-
For example: a) R. G. Brown, R. V. Chaudhar, J. M. Davidsson, J. Chem. Soc. Dalton Trans. 1977, 176; b) B. M. Trost, P. J. Metzner, J. Am. Chem. Soc. 1980, 102, 3572; J. E. Bäckvall, K. Zetterberg, B. Åkermark, in Inorganic Reactions and Methods (Ed.: A. P. Hagen), VCH. Weinheim 1991, Vol. 12A, pp. 123; D. R. Chrisope, P. Beak, W. H. Saunders, J. Am. Chem. Soc. 1988, 110, 230.
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J. Chem. Soc. Dalton Trans.
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Brown, R.G.1
Chaudhar, R.V.2
Davidsson, J.M.3
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39
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0001091976
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For example: a) R. G. Brown, R. V. Chaudhar, J. M. Davidsson, J. Chem. Soc. Dalton Trans. 1977, 176; b) B. M. Trost, P. J. Metzner, J. Am. Chem. Soc. 1980, 102, 3572; J. E. Bäckvall, K. Zetterberg, B. Åkermark, in Inorganic Reactions and Methods (Ed.: A. P. Hagen), VCH. Weinheim 1991, Vol. 12A, pp. 123; D. R. Chrisope, P. Beak, W. H. Saunders, J. Am. Chem. Soc. 1988, 110, 230.
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J. Am. Chem. Soc.
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Trost, B.M.1
Metzner, P.J.2
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40
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0003064984
-
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Ed.: A. P. Hagen, VCH. Weinheim
-
For example: a) R. G. Brown, R. V. Chaudhar, J. M. Davidsson, J. Chem. Soc. Dalton Trans. 1977, 176; b) B. M. Trost, P. J. Metzner, J. Am. Chem. Soc. 1980, 102, 3572; J. E. Bäckvall, K. Zetterberg, B. Åkermark, in Inorganic Reactions and Methods (Ed.: A. P. Hagen), VCH. Weinheim 1991, Vol. 12A, pp. 123; D. R. Chrisope, P. Beak, W. H. Saunders, J. Am. Chem. Soc. 1988, 110, 230.
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(1991)
Inorganic Reactions and Methods
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Bäckvall, J.E.1
Zetterberg, K.2
Åkermark, B.3
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41
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0003185744
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-
For example: a) R. G. Brown, R. V. Chaudhar, J. M. Davidsson, J. Chem. Soc. Dalton Trans. 1977, 176; b) B. M. Trost, P. J. Metzner, J. Am. Chem. Soc. 1980, 102, 3572; J. E. Bäckvall, K. Zetterberg, B. Åkermark, in Inorganic Reactions and Methods (Ed.: A. P. Hagen), VCH. Weinheim 1991, Vol. 12A, pp. 123; D. R. Chrisope, P. Beak, W. H. Saunders, J. Am. Chem. Soc. 1988, 110, 230.
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J. Am. Chem. Soc.
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Chrisope, D.R.1
Beak, P.2
Saunders, W.H.3
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45
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2642649705
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E. N. Frankel, W. K. Ruhwedder, W. E. Neff, D. Weisleder, J. Org. Chem. 1975, 40, 3272.
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Frankel, E.N.1
Ruhwedder, W.K.2
Neff, W.E.3
Weisleder, D.4
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47
-
-
2642609638
-
-
This is of importance since a (π-allyl) intermediate would yield allylic acetates from the attack of the acetate nucleophile at Cl and C3, whereas in acetoxypalladation the acetoxylation occurs at Cl and C2 (see Scheme 2)
-
This is of importance since a (π-allyl) intermediate would yield allylic acetates from the attack of the acetate nucleophile at Cl and C3, whereas in acetoxypalladation the acetoxylation occurs at Cl and C2 (see Scheme 2).
-
-
-
-
48
-
-
0001039476
-
-
B. Åkermark, S. Hansson, T. Rein, J. Vågberg, A. Heumann, J. E. Bäckvall, J. Organomet. Chem. 1989, 369, 433.
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Bäckvall, J.E.6
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49
-
-
2642677026
-
-
See refs [5-10]
-
a) See refs [5-10];
-
-
-
-
50
-
-
2642613843
-
-
unpublished results from our laboratory
-
b) H. Grennberg, unpublished results from our laboratory.
-
-
-
Grennberg, H.1
-
52
-
-
85088085201
-
-
1H NMR spectroscopy
-
1H NMR spectroscopy.
-
-
-
-
55
-
-
2642706040
-
-
See the Experimental Section
-
See the Experimental Section.
-
-
-
-
56
-
-
2642639795
-
-
A 1:1 mixture of allylic acetate (2 and 3) and bis-allylic diacetate (15 and 16) was obtained
-
A 1:1 mixture of allylic acetate (2 and 3) and bis-allylic diacetate (15 and 16) was obtained.
-
-
-
-
57
-
-
2642614719
-
-
With this oxidation system, numerous additional products were observed by capillary GLC. No attempt at isolation or identification of these side-products was made
-
With this oxidation system, numerous additional products were observed by capillary GLC. No attempt at isolation or identification of these side-products was made.
-
-
-
-
59
-
-
2642673765
-
-
suggested that a chloro complex reacts by different reaction pathways than does the corresponding acetato complex. See ref. [14b]
-
Wolfe et al. suggested that a chloro complex reacts by different reaction pathways than does the corresponding acetato complex. See ref. [14b].
-
-
-
Wolfe1
-
60
-
-
0000224924
-
-
For example: a) L. E. Overman, F. M. Knoll. Tetrahedron Lett. 1979, 321; b) J. Clayden, E. W. Collington, S. Warren, ibid, 1992, 33, 7039; P. M. Henry, J. Am. Chem. Soc. 1972, 94, 5200; L. E. Overman, Angew. Chem. 1984, 96, 565; Angew. Chem. Int. Ed. Engt. 1984, 23, 579.
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Tetrahedron Lett.
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Overman, L.E.1
Knoll, F.M.2
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61
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0026452042
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-
For example: a) L. E. Overman, F. M. Knoll. Tetrahedron Lett. 1979, 321; b) J. Clayden, E. W. Collington, S. Warren, ibid, 1992, 33, 7039; P. M. Henry, J. Am. Chem. Soc. 1972, 94, 5200; L. E. Overman, Angew. Chem. 1984, 96, 565; Angew. Chem. Int. Ed. Engt. 1984, 23, 579.
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Clayden, J.1
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Warren, S.3
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62
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0001424487
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For example: a) L. E. Overman, F. M. Knoll. Tetrahedron Lett. 1979, 321; b) J. Clayden, E. W. Collington, S. Warren, ibid, 1992, 33, 7039; P. M. Henry, J. Am. Chem. Soc. 1972, 94, 5200; L. E. Overman, Angew. Chem. 1984, 96, 565; Angew. Chem. Int. Ed. Engt. 1984, 23, 579.
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J. Am. Chem. Soc.
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Henry, P.M.1
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63
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0000430736
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-
For example: a) L. E. Overman, F. M. Knoll. Tetrahedron Lett. 1979, 321; b) J. Clayden, E. W. Collington, S. Warren, ibid, 1992, 33, 7039; P. M. Henry, J. Am. Chem. Soc. 1972, 94, 5200; L. E. Overman, Angew. Chem. 1984, 96, 565; Angew. Chem. Int. Ed. Engt. 1984, 23, 579.
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Angew. Chem.
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Overman, L.E.1
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64
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84985634168
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For example: a) L. E. Overman, F. M. Knoll. Tetrahedron Lett. 1979, 321; b) J. Clayden, E. W. Collington, S. Warren, ibid, 1992, 33, 7039; P. M. Henry, J. Am. Chem. Soc. 1972, 94, 5200; L. E. Overman, Angew. Chem. 1984, 96, 565; Angew. Chem. Int. Ed. Engt. 1984, 23, 579.
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Angew. Chem. Int. Ed. Engt.
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, pp. 579
-
-
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65
-
-
85088083838
-
-
2 (see ref. [14a])
-
2 (see ref. [14a]).
-
-
-
-
69
-
-
85088084520
-
-
note
-
II (see ref. [28]).
-
-
-
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70
-
-
26944488411
-
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J. E. Bäckvall, S. E. Byström, R. E. Nordberg, J. Org. Chem. 1984, 49, 4619.
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Bäckvall, J.E.1
Byström, S.E.2
Nordberg, R.E.3
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71
-
-
2642703607
-
-
Wiley Intcrscience, NY
-
Such rearrangements with a number of metal catalysts have been discussed. See for example: a) G. W. Parshall, S. D. Ittel, in Homo genons Catalysis; the Application and Chemistry of Catalysis by Soluble Transistion Metals. 2nd ed, Wiley Intcrscience, NY 1992, pp.14; b) H. G. Tange, D. G. Sherrington, J. Mol Catal. 1994, 94, 7.
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(1992)
Homo Genons Catalysis; the Application and Chemistry of Catalysis by Soluble Transistion Metals. 2nd Ed
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-
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Parshall, G.W.1
Ittel, S.D.2
-
72
-
-
0028545286
-
-
Such rearrangements with a number of metal catalysts have been discussed. See for example: a) G. W. Parshall, S. D. Ittel, in Homo genons Catalysis; the Application and Chemistry of Catalysis by Soluble Transistion Metals. 2nd ed, Wiley Intcrscience, NY 1992, pp.14; b) H. G. Tange, D. G. Sherrington, J. Mol Catal. 1994, 94, 7.
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J. Mol Catal.
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Tange, H.G.1
Sherrington, D.G.2
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74
-
-
85088086087
-
-
1H NMR integrals of H1, H2, and H3 has a value less than that expected from the amount of deuterium in the substrate
-
1H NMR integrals of H1, H2, and H3 has a value less than that expected from the amount of deuterium in the substrate.
-
-
-
-
75
-
-
2642607194
-
-
The results do not suggest the involvement of an acetoxypalladation
-
The results do not suggest the involvement of an acetoxypalladation.
-
-
-
-
77
-
-
2642674602
-
-
note
-
Under these conditions, that is in the presence of strong acid, a control experiment with 7 showed that some isomerization to 8 by an 1,3- allylic transposition occurs parallel to the rearrangement of allylic to homoallylic acetate. Therefore, the labeling experiments under these conditions can not be used as strong evidence for the (π-allyl) pathway.
-
-
-
-
78
-
-
2642642299
-
-
Minor formation of 1,4-diacetate 12 was observed
-
Minor formation of 1,4-diacetate 12 was observed.
-
-
-
-
79
-
-
0000300566
-
-
F. Bökman, A. Gogoll, L. G. M. Pettersson, O. Bohman, H. O. G. Siegbahn, Organometallics 1992, 11, 1784.
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Bökman, F.1
Gogoll, A.2
Pettersson, L.G.M.3
Bohman, O.4
Siegbahn, H.O.G.5
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