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Issue 14, 2017
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Thiyl radical-mediated cyclization of ω-alkynyl O-tert-butyldiphenylsilyloximes

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Abstract

ω-Alkynyl O-tert-butyldiphenylsilyloximes, upon treatment with odorless 4-tert-butylbenzenethiol in the presence of azobisisobutyronitrile (AIBN) in refluxing benzene, underwent addition of a thiyl radical to the alkynyl group followed by radical cyclization of the corresponding vinyl radical onto the O-silyloxime moiety to give cyclic O-silylhydroxylamines in good yields. The reactivity of O-silyloximes in radical cyclization was similar to or even higher than that of O-benzyloximes. Facile removal of the silyl group of the cyclization products leading to hydroxylamines and nitrone formation of the hydroxylamines were also demonstrated.

Graphical abstract: Thiyl radical-mediated cyclization of ω-alkynyl O-tert-butyldiphenylsilyloximes

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Publication details

The article was received on 06 Feb 2017, accepted on 06 Mar 2017 and first published on 06 Mar 2017


Article type: Paper
DOI: 10.1039/C7OB00279C
Citation: Org. Biomol. Chem., 2017,15, 3025-3034
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    Thiyl radical-mediated cyclization of ω-alkynyl O-tert-butyldiphenylsilyloximes

    N. Shibata, T. Tsuchiya, Y. Hashimoto, N. Morita, S. Ban and O. Tamura, Org. Biomol. Chem., 2017, 15, 3025
    DOI: 10.1039/C7OB00279C

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