No.105
Ketene Equivalent
| A1477 | 2-Acetoxyacrylonitrile (1) |
5g |
Generally, ketenes react with conjugate dienes by [2+2] cycloaddition so that the Diels-Alder adducts are not obtained. The reagent 1 is a ketene equivalent that undergoes the Diels-Alder reaction with a variety of dienes. For example, 1 reacts thermally with cyclopentadiene to yield a cycloadduct which upon treatment with base produces norbornenone1a). Furthermore, 1 also reacts with substitute furanes and this reaction has been used for the synthesis of sesquiterpene which is a family of biologically active natural products1b).
References
1) Diels-Alder reactions
a) P. D. Bartlett, B. E. Tate, J. Am. Chem. Soc., 78, 2473 (1956).
b) D. S. Brown, L. A. Paquette, J. Org. Chem., 57, 4512 (1992).
2) Review
S. Ranganathan, D. Ranganathan, A. K. Mehrotra, Synthesis, 1977, 289.
3) Other reactions
a) A. Oku, T. Yokoyama, T. Harada, J. Org. Chem., 48, 5333 (1983).
b) A. Padwa, D. N. Kline, K. F. Koehler, M. Matzinger, M. K. Venkatramanan,
J. Org. Chem., 52, 3909 (1987).
c) W. L. Dilling, R. D. Kroening, J. C. Little, J. Am. Chem. Soc., 92, 928 (1970).
a) P. D. Bartlett, B. E. Tate, J. Am. Chem. Soc., 78, 2473 (1956).
b) D. S. Brown, L. A. Paquette, J. Org. Chem., 57, 4512 (1992).
2) Review
S. Ranganathan, D. Ranganathan, A. K. Mehrotra, Synthesis, 1977, 289.
3) Other reactions
a) A. Oku, T. Yokoyama, T. Harada, J. Org. Chem., 48, 5333 (1983).
b) A. Padwa, D. N. Kline, K. F. Koehler, M. Matzinger, M. K. Venkatramanan,
J. Org. Chem., 52, 3909 (1987).
c) W. L. Dilling, R. D. Kroening, J. C. Little, J. Am. Chem. Soc., 92, 928 (1970).
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