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A variation of Favorskii rearrangement mechanism under weakly acidic conditions_the case of clobetasol propionate degradation in solution.pdf (813.35 kB)
A Variation of Favorskii Rearrangement Mechanism Under Weakly Acidic Conditions: The Case of Clobetasol Propionate Degradation in Solution
Preprints are manuscripts made publicly available before they have been submitted for formal peer review and publication. They might contain new research findings or data. Preprints can be a draft or final version of an author's research but must not have been accepted for publication at the time of submission.
submitted on 05.02.2020 and posted on 06.02.2020by Yun Tian, Haoran Zhang, Zach Zhu, Li Chen, Evelyn Wang, Jianyang Jin, Dan Li, Wenquan Zhu, Min Li, Lei Fu
This paper describes our efforts in proposing a novel mechanism for the
formation of the major degradant of clobetasol propionate under weakly acidic
conditions through a comprehensive investigation. In the proposed mechanism, the
key Favorskii intermediate plays a critical role. This variation of the
original Favorskii rearrangement, which proceeds only under alkaline conditions, has
not been reported before. This mechanism enriches the understanding of
the degradation chemistry of corticosteroids containing the α-haloketone
moiety on their 17-position.