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Neighbouring group participation in the allylic oxidation of a Δ5-steroid

✍ Scribed by James R. Hanson; Paul B. Reese; Ian H. Sadler

Publisher
Elsevier Science
Year
1982
Tongue
French
Weight
162 KB
Volume
23
Category
Article
ISSN
0040-4039

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✦ Synopsis

Labellang studies show that thas involves the mlgratlon of the 31-acetoxyl group and an overall retention of configuration at G4.

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2H, '% and l4 C-Labelling studies are presented as evidence for the intervention of the jk-hydroxyl group, possibly via a 3fi,4.&acetoxylinium ion in the rearrangement and acetylation of @-hydroxy-4/-acetoxy\_d-steroids by glacial acetic acid to fonn 3/,6&diaoetov-k-steroids. The allylic rearrangem