Abstract
THE formula of ethylene oxide is commonly portrayed as (I), the instability of the compound being ascribed to the existence of strain tending to open the ring. This explanation can scarcely be accepted, for, if it were true, the compound (II), with less angular strain, should be more stable—which it is not. Zimakov1 has recently directed attention to this point and to the discrepancy between the structure (I) and the observed properties of ethylene oxide. He points out that the latter (for example, polymerization, addition reactions) strongly suggest a resemblance of structure to ethylene, and proposes to replace (I) by a resonance hybrid of (II), (III) and (IV).
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References
Zimakov, Acta Phys. Chim. U.S.S.R., 31, 401 (1946).
Walsh, J. Chem. Soc., in the press.
Dewar, J. Chem. Soc., 406, 777 (1946).
Sugden, Walsh and Price, Nature, 148, 372 (1941).
Rogers and Roberts, J. Amer. Chem. Soc., 68, 843 (1940).
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WALSH, A. Structures of Ethylene Oxide and Cyclopropane. Nature 159, 165 (1947). https://doi.org/10.1038/159165a0
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DOI: https://doi.org/10.1038/159165a0
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