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For reviews, see: (a) Ghosez, L.; Marchand-Brynaert, J. In Comprehensive Organic Chemistry; Pergamon: Oxford, England, 1991; Vol 5, p 85. (b) Wolfe, J. F.; Ogliaruso, M. A. In The Chemistry of Functional Groups, Supplement B: The Chemistry of Acid Derivatives Part 2; John Wiley and Sons: New York, 1979; p 1231.
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For [2 + 2] cycloaddition of ketene with imine, see: (a) Matsui, S.; Hashimoto, Y.; Saigo, K. Synthesis 1998, 1161. (b) Georg, G. I.; Mashava, P. M.; Guan, X. Tetrahedron Lett. 1991, 32, 581. (c) Amin, S. G.; Glazer, R. D.; Manhas, M. S. Synthesis 1979, 210. For intramolecular [2 + 2] cycloaddition of ketene with olefin, see: (d) Funk, R. L.; Abelman, M. M.; Jellison, K. M. Synlett 1989, 36.
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Synthesis
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Matsui, S.1
Hashimoto, Y.2
Saigo, K.3
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13
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0026088008
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For [2 + 2] cycloaddition of ketene with imine, see: (a) Matsui, S.; Hashimoto, Y.; Saigo, K. Synthesis 1998, 1161. (b) Georg, G. I.; Mashava, P. M.; Guan, X. Tetrahedron Lett. 1991, 32, 581. (c) Amin, S. G.; Glazer, R. D.; Manhas, M. S. Synthesis 1979, 210. For intramolecular [2 + 2] cycloaddition of ketene with olefin, see: (d) Funk, R. L.; Abelman, M. M.; Jellison, K. M. Synlett 1989, 36.
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Tetrahedron Lett.
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Georg, G.I.1
Mashava, P.M.2
Guan, X.3
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14
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0018378294
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For [2 + 2] cycloaddition of ketene with imine, see: (a) Matsui, S.; Hashimoto, Y.; Saigo, K. Synthesis 1998, 1161. (b) Georg, G. I.; Mashava, P. M.; Guan, X. Tetrahedron Lett. 1991, 32, 581. (c) Amin, S. G.; Glazer, R. D.; Manhas, M. S. Synthesis 1979, 210. For intramolecular [2 + 2] cycloaddition of ketene with olefin, see: (d) Funk, R. L.; Abelman, M. M.; Jellison, K. M. Synlett 1989, 36.
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Synthesis
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Amin, S.G.1
Glazer, R.D.2
Manhas, M.S.3
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15
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85023361751
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For [2 + 2] cycloaddition of ketene with imine, see: (a) Matsui, S.; Hashimoto, Y.; Saigo, K. Synthesis 1998, 1161. (b) Georg, G. I.; Mashava, P. M.; Guan, X. Tetrahedron Lett. 1991, 32, 581. (c) Amin, S. G.; Glazer, R. D.; Manhas, M. S. Synthesis 1979, 210. For intramolecular [2 + 2] cycloaddition of ketene with olefin, see: (d) Funk, R. L.; Abelman, M. M.; Jellison, K. M. Synlett 1989, 36.
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(1989)
Synlett
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Funk, R.L.1
Abelman, M.M.2
Jellison, K.M.3
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0029550884
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Inouye, M.1
Miyake, T.2
Furusyo, M.3
Nakazumi, H.4
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17
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85034464742
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note
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-1) 1760, 1680.
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19
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85034483964
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note
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The procedure for the polymerization reaction is similar to that for the model reaction, in which bisimine 3 (0.330 mmol) was used instead of 0.660 mmol of imine 2. After the reaction mixture was stirred at 20 °C for 48 h, the mixture was filtered and concentrated under reduced pressure. The resultant mixture was dissolved in DMF (10 mL) and precipitated with 1 M aqueous HCl (100 mL) to obtain the corresponding polymer 7, which was collected by filtration with suction and dried under vacuum.
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