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Reviewed in: Tidwell, T. T. Ketenes; Wiley: New York, 1991.
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(b) Loebach, J. L.; Bennett, D. M.; Danheiser, R. L. J. Org. Chem. 1998, 63, 8380.
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Bennett, D.M.2
Danheiser, R.L.3
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33748664864
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For reviews on the chemistry of silylketenes, see ref 1 and the following: (a) Pommier, A.; Kocienski, P.; Pons, J.-M. J. Chem. Soc., Perkin Trans. 1 1998, 13, 2105.
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Pons, J.-M.3
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(b) Schaumann, E.; Scheiblich, S. In Methoden der Organischen Chemie (Houben-Weyl); Kropf, E., Schaumann, E., Eds.; Thieme: Stuttgart, Germany, 1993; Vol. E15, Part 2.
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Schaumann, E.1
Scheiblich, S.2
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11
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0000943554
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For related reactions involving silylated bisketenes, see: Colomvakos, J. D.; Egle, I.; Ma, J.; Pole, D. L.; Tidwell, T. T.; Warkentin, J. J. Org. Chem. 1996, 61, 9522.
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Egle, I.2
Ma, J.3
Pole, D.L.4
Tidwell, T.T.5
Warkentin, J.6
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(b) Brückmann, R.; Schneider, K.; Maas, G. Tetrahedron 1989, 45, 5517.
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Brückmann, R.1
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14
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0001725065
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(a) Danheiser, R. L.; Miller, R. F.; Brisbois, R. G.; Park, S. Z. J. Org. Chem. 1990, 55, 1959.
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(b) Danheiser, R. L.; Miller, R. F.; Brisbois, R. G. Org. Synth. 1995, 73, 134.
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Wiley: New York, Collect.
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(c) Danheiser, R. L.; Savariar, S.; Cha, D. D. Organic Syntheses; Wiley: New York, 1993; Collect. Vol. VIII, pp 82-86.
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Cha, D.D.3
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Heterodienophile additions to dienes
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Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford
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(c) Weinreb, S. M. Heterodienophile Additions to Dienes. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, p 401.
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Weinreb, S.M.1
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22
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85034152622
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note
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13C NMR, and elemental analyses were fully consistent with the assigned structures (see Supporting Information).
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23
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85034143503
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note
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4NF in THF (25 °C, 30 min) led to a complex mixture of products.
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25
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0000998435
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(a) Barluenga. J.; Aznar, F.; Valdés, C.; Cabal, M.-P. J. Org. Chem. 1993, 58, 3391.
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Aznar, F.2
Valdés, C.3
Cabal, M.-P.4
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0000651283
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(b) Barleunga, J.; Aznar, F.; Valdés. C.; Martín, A.; García-Granda, S.; Martin, E. J. Am. Chem. Soc. 1993, 115, 4403.
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Barleunga, J.1
Aznar, F.2
Valdés, C.3
Martín, A.4
García-Granda, S.5
Martin, E.6
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27
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85034145841
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note
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1H NMR difference NOE experiments.
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28
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0002674759
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Georg, G. I., Ed.; VCH: New York
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For a review on [2 + 2] cycloadditions of imines and ketenes, see: Georg, G. I.; Ravikumar, V. T. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH: New York, 1993; pp 295-368.
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The Organic Chemistry of β-Lactams
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Georg, G.I.1
Ravikumar, V.T.2
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29
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0000869472
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and references therein
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The [2 + 2] cycloaddition of N-silyl imines with silylketenes has not been reported previously, although Staudinger reactions of silyl imines with ketenes (generated by dehydrochlorination of acyl chlorides) have been studied extensively by Panunzio and co-workers. See: Bacchi, S.; Bongini, A.; Panunzio, M.; Villa, M. Synlett 1998, 843 and references therein.
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Synlett
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Bacchi, S.1
Bongini, A.2
Panunzio, M.3
Villa, M.4
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