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Steroids and steroidases—XIX

1973; Elsevier BV; Volume: 29; Issue: 14 Linguagem: Inglês

10.1016/0040-4020(73)80128-0

1464-5416

J. Bryan Jones, Philip B. Price,

Steroid Chemistry and Biochemistry

Quantitative comparisons of the product ratios of the mechanistically similar diazomethane and Tiffeneau-Demjanov homologations of 17β-hydroxy-5α-androstan-3-one and 5α-cholestan-3-one have shown that equatorial approach of diazomethane to the C-3 CO group predominates to the extent of 70–79%. The data for both the C-17β-OH and -C8H17 substituted steroids are in close agreement thereby confirming that the C-17 substituents do not exert any significant long range effect on the reactions studied.