Bis(2,4,6-tri-tert-butylphenyl)bicyclotetraphosphane

✍ Scribed by Ralf Riedel; Dr. Hans-Dieter Hausen; Prof. Dr. Ekkehard Fluck

• Publisher: John Wiley and Sons
• Year: 1985
• Tongue: English
• Weight: 269 KB
• Volume: 24
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/anie.198510561

✦ Synopsis

pounds, presumably oligomers. In glacial acetic acid (CH3C0,H/CH2C12=3 :2, i=40 mA/cm2, T=2OoC, Pt electrode) 17% androstanyl acetate is obtained and 38% androstane is recovered. Remarkable is the selectivity of the oxidation: We found that the 6-(6a), 7-, and 12-acetates are formed in the ratio 35 : 1 : 2 S ; other acetates could not be detected by us. Assignment of the structures was accomplished by hydrolysis, oxidation to the ketone, and comparison of the mass spectra with those given in the literature. The main product was characterized ',C-NMR spectroscopically as 6a-acetoxy-5a-androstane (6a). The electrolysis in methanol (methanol/dichloromethane, 0.1 M NaCIO,, glassy carbon electrode) proceeds even more selectively. At a 53% conversion (47% androstane recovered) 14% 6-methoxyandrostane (7a) and 27% 6-(methoxymethoxy)androstane (Sa) were formed.