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Synthesis of multisubstituted phenols by formal [4 + 2] cycloaddition of nucleophilic alkynes with 3-ethoxycyclobutanones

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Abstract

Nucleophilic alkynes bearing sulfonamide, trimethylsilyl, or p-methoxyphenyl groups at the sp carbon reacted with 3-ethoxycyclobutanones to give formal [4 + 2] cycloadducts by activation with TiCl4. Reactions with 2-monoalkyl and 2-nonsubstituted 3-ethoxycyclobutanones gave phenol derivatives directly by benzannulation, while the use of 2,2-dimethyl-3-ethoxycyclobutanone gave the corresponding dienones, which were converted to pentasubstituted phenols by dienone-phenol rearrangement. Regioselectivity that depended on the activation conditions of dienone-phenol rearrangement is also described.

Graphical abstract: Synthesis of multisubstituted phenols by formal [4 + 2] cycloaddition of nucleophilic alkynes with 3-ethoxycyclobutanones

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Publication details

The article was received on 03 Apr 2017, accepted on 05 Jun 2017 and first published on 05 Jun 2017


Article type: Communication
DOI: 10.1039/C7OB00827A
Citation: Org. Biomol. Chem., 2017, Advance Article
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    Synthesis of multisubstituted phenols by formal [4 + 2] cycloaddition of nucleophilic alkynes with 3-ethoxycyclobutanones

    T. Kuzuguchi, Y. Yabuuchi, T. Yoshimura and J. Matsuo, Org. Biomol. Chem., 2017, Advance Article , DOI: 10.1039/C7OB00827A

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