Issue 8, 2002
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Self-terminating, oxidative radical cyclizations of medium-sized cycloalkynones with inorganic and organic oxygen-centered radicals of type XO˙: the reaction pathway depends on the nature of X

Uta Wille*a  and  Christian Jargstorffa  

* Corresponding authors

a Institut für Organische Chemie der Christian-Albrechts-Universität zu Kiel, Olshausenstr. 40, 24098 Kiel, Germany
E-mail: uwille@oc.uni-kiel.de
Fax: ++49-(0)431-8801558
Tel: ++49-(0)431-8801179

Abstract

The reaction of various inorganic and organic oxygen-centered radicals of type XO˙ with cyclodec-5-ynone 6 can be used as a mechanistic probe to study the ease with which X˙ acts as a leaving group in self-terminating, oxidative radical cyclizations. It was observed that when X˙ has good leaving ability the reaction leads to formation of the bicyclic epoxy ketones 13 and 14, whereas in the other cases a competition between the individual reversible cyclization steps resulted in predominant formation of the spiro ketone 20. The experimental data obtained lead to the suggestion that vinyl radicals could rearrange through 1,2-group migrations.

Graphical abstract: Self-terminating, oxidative radical cyclizations of medium-sized cycloalkynones with inorganic and organic oxygen-centered radicals of type XO˙: the reaction pathway depends on the nature of X

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Article information

DOI
https://doi.org/10.1039/B201672A
Article type
Paper
Submitted
18 Feb 2002
Accepted
08 Mar 2002
First published
26 Mar 2002

J. Chem. Soc., Perkin Trans. 1, 2002, 1036-1041

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Self-terminating, oxidative radical cyclizations of medium-sized cycloalkynones with inorganic and organic oxygen-centered radicals of type XO˙: the reaction pathway depends on the nature of X

U. Wille and C. Jargstorff, J. Chem. Soc., Perkin Trans. 1, 2002, 1036 DOI: 10.1039/B201672A

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