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Issue 12, 1994
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Formation of 18-nor-13(14)-ene-17β-methyl steroids during perfluoroacylation of anabolic steroids bearing a tertiary 17-hydroxy group and compounds related to corticosteroids

Dietmar Stöckl,  Roland de Sagher,  Linda M. Thienpont,  Greet Debruyckere  and  Carlos H. Van Peteghem 

Abstract

The results of derivatization (for gas chromatography–mass spectrometry) of steroids bearing a tertiary 17-hydroxy group with perfluoroacyl anhydrides in acetone are presented. The reaction products are investigated by using low- and high-resolution mass spectrometry, metastable ion measurements, and proton and carbon-13 nuclear magnetic resonance spectroscopy. On the basis of the results, we conclude that all the products lose the 17-hydroxy group during derivatization and undergo a Wagner–Meerwein rearrangement to give 18-nor-13(14)-ene-17β-methyl steroids.

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Article type: Paper
DOI: 10.1039/AN9941902587
Citation: Analyst, 1994,119, 2587-2590
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    Formation of 18-nor-13(14)-ene-17β-methyl steroids during perfluoroacylation of anabolic steroids bearing a tertiary 17-hydroxy group and compounds related to corticosteroids

    D. Stöckl, R. de Sagher, L. M. Thienpont, G. Debruyckere and C. H. Van Peteghem, Analyst, 1994, 119, 2587
    DOI: 10.1039/AN9941902587

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