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Skeletal rearrangement of 6,8-dioxabicyclo[3.2.1]octan-4-ols promoted by thionyl chloride or Appel conditions

A skeletal rearrangement of a series of 6,8-dioxabicyclo[3.2.1]octan-4-ols has been developed using SOCl2 in the presence of pyridine. An oxygen migration from C5 to C4 was observed when the C4 alcohols were treated with SOCl2/pyridine, giving a 2-chloro-3,8-dioxabicyclo[3.2.1]octane ring-system via...

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Principais autores: Martyn Jevric, Julian Klepp, Johannes Puschnig, Oscar Lamb, Christopher J. Sumby, Ben W. Greatrex
Format: Artigo
Sprog:Inglês
Udgivet: Beilstein-Institut 2024-04-01
Serier:Beilstein Journal of Organic Chemistry
Fag:
bicyclic ring
cyrene
levoglucosenone
rearrangement
thionyl chloride
Online adgang:https://doi.org/10.3762/bjoc.20.74
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