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Fission of 2: 3-Dihydropyran into Acrolein and Ethylene

Abstract

IT has been suggested1 that 2:3-dihydrbfuran (I) on heating above 400° rearranges into cyclopropane aldehyde (II). By analogy, 2: 3-dihydropyran (III) should give cyclobutane aldehyde (IV). Experiments have shown, however, that, on heating, dihydropyran does not produce this aldehyde but splits by homogeneous reaction into acrolein and ethylene (V)2. Whether the cyclic aldehyde intervenes in the reaction or not must still remain an open question.

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References

  1. Wilson, J. Chem. Soc., 59 (1945).

  2. Wilson, Brit. P., 569625. Cf., also, Bremner and Jones, Brit. P., 573507.

  3. Kline and Turkevich, J. Amer. Chem. Soc., 67, 498 (1945).

    Article  CAS  Google Scholar 

  4. Paul, R., private communication.

  5. Bremner and McNeil, Brit. P., 547334.

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WILSON, C. Fission of 2: 3-Dihydropyran into Acrolein and Ethylene. Nature 157, 846 (1946). https://doi.org/10.1038/157846b0

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