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8
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0033598241
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For other recent examples of O→C rearrangements, see: (a) Smith, A. B., III; Verhoest, P. R.; Minbiole, K. P.; Lim, J. J. Org. Lett. 1999, 1, 909.
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Smith III, A.B.1
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Lim, J.J.4
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0033598242
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(b) Smith, A. B., III; Minbiole, K. P.; Verhoest, P. R.; Beauchamp, T. J. Org. Lett. 1999, 1, 913.
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Smith III, A.B.1
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10
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0034677084
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(c) Sollogoub, M.; Mallet, J.-M.; Sinay, P. Angew. Chem., Int. Ed. 2000, 39, 362.
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Sollogoub, M.1
Mallet, J.-M.2
Sinay, P.3
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11
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0034697707
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(d) Buffet, M. F.; Dixon, D. J.; Edwards, G. L.; Ley, S. V.; Tate, E. W. J. Chem. Soc., Perkin Trans, 1 2000, 1815.
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Buffet, M.F.1
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Ley, S.V.4
Tate, E.W.5
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12
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0037151613
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(e) Zhang, Y.; Reynolds, N. T.; Manju, K.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 9720.
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Zhang, Y.1
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Rovis, T.4
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13
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0001573041
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Brown, D. S.; Bruno, M.; Davenport, R. J.; Ley, S. V. Tetrahedron 1989, 45, 4293.
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Brown, D.S.1
Bruno, M.2
Davenport, R.J.3
Ley, S.V.4
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14
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-
33748726149
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Ley, S. V.; Humphries, A. C.; Eick, H.; Downham, R.; Ross, A. R.; Boyce, R. J.; Pavey, J. B. J.; Pietruszka, J. J. Chem. Soc., Perkin Trans, 1 1998, 3907.
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Ley, S.V.1
Humphries, A.C.2
Eick, H.3
Downham, R.4
Ross, A.R.5
Boyce, R.J.6
Pavey, J.B.J.7
Pietruszka, J.8
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15
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0000692406
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Ley, S. V.; Lygo, B.; Organ, H. M.; Wonnacott, A. Tetrahedron 1985, 41, 3825.
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Ley, S.V.1
Lygo, B.2
Organ, H.M.3
Wonnacott, A.4
-
16
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-
28044437219
-
-
note
-
1H NMR spectrum. The stereochemical assignments of complexes 12 and 13 were made by analogy.
-
-
-
-
17
-
-
33845280186
-
-
The addition of Lewis acid to noncomplexed enol ether substrates did not result in rearrangement to the corresponding ketones. A mixture of recovered starting material and alkene isomerization products were obtained instead. Additionally, significant substrate conversions were only observed when > 1.0 equiv of diethylaluminium chloride was employed. Indeed, the Lewis acid character of dialkylaluminium chlorides has been found to be highly dependent on reaction stoichiometry: (a) Evans, D. A.; Chapman, K. T.; Bisaha, J. J. Am. Chem. Soc. 1988, 110, 1238.
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Evans, D.A.1
Chapman, K.T.2
Bisaha, J.3
-
18
-
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0033546101
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(b) Evans, D. A.; Allison, B. D.; Yang, M. G. Tetrahedron Lett. 1999, 40, 4457.
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Evans, D.A.1
Allison, B.D.2
Yang, M.G.3
-
20
-
-
28044435447
-
-
note
-
The identity of the major isomers of 18 and 19 was not elucidated.
-
-
-
-
21
-
-
0031436857
-
-
Jones, G. B.; Wright, J. M.; Rush, T. M.; Plourde, G. W., II; Kelton, T. F.; Mathews, J. E.; Huber, R. S.; Davidson, J. P. J. Org. Chem. 1997, 62, 9379.
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-
Jones, G.B.1
Wright, J.M.2
Rush, T.M.3
Plourde II, G.W.4
Kelton, T.F.5
Mathews, J.E.6
Huber, R.S.7
Davidson, J.P.8
-
22
-
-
27944511863
-
-
note
-
22ONa 277.1568, found 277.1556.
-
-
-
-
23
-
-
28044431888
-
-
note
-
Surprisingly, the Wittig reaction was only successful for cyclohexanone derivatives and failed to provide enol ether products when ketones of other ring sizes were employed.
-
-
-
-
27
-
-
0001573041
-
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Brown, D. S.; Bruno, M.; Davenport, R. J.; Ley, S. V. Tetrahedron 1989, 45, 4293.
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(1989)
Tetrahedron
, vol.45
, pp. 4293
-
-
Brown, D.S.1
Bruno, M.2
Davenport, R.J.3
Ley, S.V.4
-
28
-
-
28044452719
-
-
note
-
The identity of the major isomer was not elucidated.
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-
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