Competing pathway involved in allylic acetoxylation of androst-5-en-17-one, and oxidation of allylic alcohols with chromium oxides

@article{Numazawa1995CompetingPI,
  title={Competing pathway involved in allylic acetoxylation of androst-5-en-17-one, and oxidation of allylic alcohols with chromium oxides},
  author={M. Numazawa and M. Tachibana and Miyako Kamiza},
  journal={Steroids},
  year={1995},
  volume={60},
  pages={499-505}
}
  • M. Numazawa, M. Tachibana, Miyako Kamiza
  • Published 1995
  • Chemistry, Medicine
  • Steroids
  • Allylic acetoxylation of androst-5-en-17-one (1) with bromine and silver acetate gave 6 alpha- and 6 beta-acetoxyandrost-4-en-17-ones [4 (3%) and 5 (12%)] and 5 alpha-bromo-6 beta-acetoxy steroid 8 (4%) along with the expected product 4 beta-acetoxy derivative 2 (45%). Treatment of 5 alpha,6 beta-bromide 12, an intermediate of the acetoxylation reaction, with silver acetate also produced the acetates 2, 4, 5, and 8 in relative yields similar to those above. These results indicate that the 6… CONTINUE READING
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