Westphalen rearrangement. Mechanism of formation of 5α-acetoxy derivatives

Author:

Kočovský Pavel,Černý Václav,Tureček František

Abstract

5α-Acetoxy derivatives formed as by-products in the course of Westphalen rearrangement of [5-18O]-5-hydroxy-5α-cholestanes Ia and Ib are shown to preserve their 18O content. This fact rules out previously proposed neighboring group participation of the 6β-substituent involving a 5β,6β-„onium" intermediate (F).

Publisher

Institute of Organic Chemistry & Biochemistry

Subject

General Chemistry

Cited by 16 articles. 订阅此论文施引文献 订阅此论文施引文献,注册后可以免费订阅5篇论文的施引文献,订阅后可以查看论文全部施引文献

1. Westphalen's diol diacetate: 19(10→5)-abeo-5β-cholest-9-ene-3β,6β-diyl diacetate;Acta Crystallographica Section E Structure Reports Online;2012-11-10

2. Westphalen Rearrangement;Comprehensive Organic Name Reactions and Reagents;2010-09-15

3. Electrophilic Additions to Double Bonds;PATAI'S Chemistry of Functional Groups;2009-12-15

4. Bismuth(III) salt-catalyzed Westphalen and “backbone” rearrangements of 5β,6β-epoxysteroids;Steroids;2008-05

5. A Simple and Efficient Procedure for the Synthesis of Optically Active 4-Methoxy-α-Methylphenylethylamine from Tyrosine;Synthetic Communications;1998-06

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