Studies of the slowing of the dienone-phenol rearrangement of a steroidal 1,4-dien-3-one by the introduction of an 11-keto group.
It has been shown previously that steroidal 11-keto-1,4-dien-3-ones undergo dienone-phenol rearrangement significantly more slowly than their 11-deoxy-, or 11 beta-hydroxy- and 11-acetoxy analogs. We have tested the explanations suggested for this, and are able to reject most of them. There remains the probability that the 11-keto group reduces the migrating ability of the adjacent atom, C-9, which frequently migrates in steroidal rearrangements.
al-Zamil
I Z
IZ
Department of Chemistry, University of Birmingham, UK.
Waring
A J
AJ
D000736:Androstenes; D055598:Chemical Phenomena; D002621:Chemistry; D006863:Hydrogen-Ion Concentration; D007700:Kinetics; D008279:Magnetic Resonance Imaging; D015394:Molecular Structure; D013056:Spectrophotometry, Ultraviolet
D000736:Androstenes; C061692:androsta-1,4-diene-3,11,17-trione