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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 7
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Original Articles

PtCl2-Catalyzed Cyclization of o-Diethynylbenzene Derivatives Triggered by Intramolecular Nucleophilic Attack

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Pages 1077-1087 | Received 19 Dec 2009, Published online: 03 Mar 2011
 

Abstract

PtCl2-catalyzed cyclization of o-diethynylbenzene derivatives bearing a hydroxyethyl group yielded naphthofuran derivatives by initial intramolecular cyclization of the hydroxy group to an activated ethynyl group followed by attack of the second ethynyl group to a vinylplatinum intermediate. When the ethynyl terminal is substituted by a hydroxypropyl group, not only homologous naphthodihydropyran but also indenylidenetetrahydrofuran derivatives were formed.

ACKNOWLEDGMENT

This work was supported by a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science, and Technology, Japan.

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