Issue 0, 1974
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Steroids. Part XIX. Westphalen rearrangement of 6β-azido- and 6β-cyano-5α-hydroxy-steroids. Neighbouring group participation by the azido-group

Brian A. Marples,   Brian M. O'Callaghan  and  John L. Scottow  

Abstract

The 6β-azido-5α-hydroxy-compound (3) and the 6β-cyano-5α-hydroxy-compound (4) rearrange to Δ9-compounds. The major product from the azido-compound (3) is 3β,5-diacetoxy-6β-azido-5α-cholestane (11), indicating significant neighbouring group participation by the azido-group. The effect of the 6β-cyano-group on reaction rate is comparable to that of a 6β-fluoro-substituent.

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Article information

DOI
https://doi.org/10.1039/P19740001026
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1974, 1026-1028

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Steroids. Part XIX. Westphalen rearrangement of 6β-azido- and 6β-cyano-5α-hydroxy-steroids. Neighbouring group participation by the azido-group

B. A. Marples, B. M. O'Callaghan and J. L. Scottow, J. Chem. Soc., Perkin Trans. 1, 1974, 1026 DOI: 10.1039/P19740001026

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