Abstract
2,4-DINITROPHENYLHYDRAZONES have proved very useful derivatives for identification purposes, but have so far found only limited application in preparative work. This is due to the fact that there exists no general method for the regeneration of the corresponding carbonyl compounds. As Djerassi pointed out1, the failure to cleave 2,4-dinitrophenyl-hydrazones has imposed considerable limitations on the use of the Mattox–Kendall2 dehydrobromination method in the field of sterol chemistry. Thus, in the case of 2,4-dinitrophenylhydrazones of Δ4,6-dien-3-ketosteroids, only about 5–10 per cent of ketone could be recovered after treatment with pyruvic acid and hydrobromic acid, and derivatives of Δ1,4-dien-3-ketosteroids could not be split at all1.
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References
Djerassi, C., J. Amer. Chem. Soc., 71, 1003 (1949).
Mattox, V. R., and Kendall, E. C., J. Amer. Chem. Soc., 70, 882 (1948); 72, 2290 (1950).
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DEMAECKER, J., MARTIN, R. A Method for the Cleavage of 2,4-Dinitrophenylhydrazones and its Application to Steroidal Ketones. Nature 173, 266 (1954). https://doi.org/10.1038/173266a0
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DOI: https://doi.org/10.1038/173266a0
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