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Chemistry of acetals Communication 17. Study of the hydrolysis of diacetals of various types by gas-liquid chromatography

Conclusions

  1. 1.

    The hydrolysis of diacetals of glyoxal, succinaldehyde, glutaraldehyde, adipaldehyde, malealdehyde, muconaldehyde, 2,4,6-octatrienedial, and 2-butyndial with an equimolecular amount of water was studied by gasliquid chromatography.

  2. 2.

    Muconaldehyde diacetal is selectively hydrolyzed at one of the acetal groupings with formation of the monoacetal. Under the conditions of the hydrolysis malealdehyde diacetal gives 2,5-diethoxy-2,5-dihydrofuran as the main product, glutaraldehyde diacetal gives some 2, 6-diethoxytetrahydropyran and some glutaraldehyde, and the diacetals of glyoxal, succinaldehyde, adipaldehyde, and 2,4,6-octatrienedial are hydrolyzed to the dialdehydes.

  3. 3.

    The results are explained on the basis of an examination of electronic and steric factors.

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Literature cited

  1. 1.

    L. A. Yanovskaya and V. F. Kucherov, Izv. AN SSSR, Old, khim. n. 667 (1962).

  2. 2.

    L. A. Yanovskaya, B. A Rudenko, V. F. Kucherov, R. N. Stepanova, and G. A. Kogan, Izv. AN SSSR. Otd. khim. n. 2189 (1962).

  3. 3.

    L. A. Yanovskaya, V. F. Kucherov, and B. G. Kovalev, Izv. AN SSSR. Otd. khim. n. 675 (1962).

  4. 4.

    L. A. Yanovskaya, B. G. Kovalev, and V. F. Kucherov, Izv. AN SSSR. Otd. khim. n 684 (1965).

  5. 5.

    V. F. Kucherov, L. A. Yanovskaya, and B. G. Kovalev, Dokl. AN SSSR,133, 370 (1960).

  6. 6.

    L. A. Yanovskaya, R. N. Stepanova, G. A. Kogan, and V. F. Kucherov, Izv. AN SSSR. Otd. khim. n. 857 (1963).

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Additional information

Translated from Izvestiya Akadeemii Nauk SSSR, Seriya Khimicheskaya, No. 8, pp. 1416–1424, August, 1965 Original article submitted June 25, 1963

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Yanovskaya, L.A., Stepanova, R.N. Chemistry of acetals Communication 17. Study of the hydrolysis of diacetals of various types by gas-liquid chromatography. Russ Chem Bull 14, 1376–1382 (1965). https://doi.org/10.1007/BF00846196

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Keywords

  • Acetal
  • Chromatography
  • Hydrolysis
  • Glutaraldehyde
  • Main Product