Syntheses and Reactivity of Naphthalenyl-Substituted Arenediynes

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• 作者：Nadezhda V. Korovina ; Michael L. Chang ; Trang T. Nguyen ; Ramiro Fernandez ; Heather J. Walker ; Marilyn M. Olmstead ; Benjamin F. Gherman ; John D. Spence
• 刊名：Organic Letters
• 出版年：2011
• 出版时间：July 15, 2011
• 年：2011
• 卷：13
• 期：14
• 页码：3660-3663
• 全文大小：715K
• 年卷期：v.13,no.14(July 15, 2011)
• ISSN：1523-7052

文摘

A series of naphthalenyl-substituted arenediynes were prepared to examine photochemical reactivity. For naphthalen-1-ylethynyl arenediyne, 350 nm photolysis resulted in a tandem [2 + 2] photocycloaddition to afford cyclobutene adducts. For naphthalen-2-ylethynyl derivatives, electron-donating methoxy substituents were found to facilitate C¹鈥揅⁶ Bergman cyclization at 300 nm. Theoretical calculations provided further insight into thermal and photochemical reactivity.