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Synthesis of Testosterones from Estrogens

✍ Scribed by Dr. H. D. Berndt; Priv.-Doz. Dr. R. Wiechert

Publisher
John Wiley and Sons
Year
1969
Tongue
English
Weight
263 KB
Volume
8
Category
Article
ISSN
0044-8249

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✦ Synopsis

Not only many organic N-sulfinylamines [ I ] but also N-(trimethylsilyl)sulfinylamine[zl are known, the reactions of the latter being very similar to those of silyl pseudohalides. We have obtained bis(sulfinylamido)mercury(II) ( I ) as the first sulfinylamide of a metal by reaction of mercury(i1) fluoride with N-(trimethylsily1)sulfinylamine. The reaction proceeds quantitatively.

Tetrahydrofuran is a particularly suitable solvent as ( I ) dissolves readily in it and can be recrystallized from it. 23 g of HgFz reacts with 27 g of (CH&SiNSO in 40-60 ml of boiling, stirred, dry T H F within 30 rnin in a strongly exothermic reaction. The amide ( I ) crystallizes as colorless needles, m.p. 128 "C (decomp.), but, if heating is too slow, decomposition sets in below the melting point. In contrast to most organic sulfinylamines, it is surprisingly stable to hydrolysis and alcoholysis. Compound ( I ) was identified by analysis and its mass spec-trumr31 [with reference to the isotope 202Hg: m / e = 326,

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