Diels-Alder reaction of tropones with arynes: Synthesis of functionalized benzobicyclo[3.2.2]nonatrienones

Manikandan Thangaraj, Sachin Suresh Bhojgude, Rajesh H. Bisht, Rajesh G. Gonnade, Akkattu T. Biju

Research output: Contribution to journalArticlepeer-review

44 Scopus citations

Abstract

A new procedure for the mild, practical, and scalable Diels-Alder reaction of tropones with arynes is reported. Differently substituted tropones undergo selective [4 + 2] cycloaddition with arynes generated in situ by the fluoride-induced 1,2-elimination of 2-(trimethylsilyl)aryl triflates, allowing the formation of functionalized benzobicyclo[3.2.2]nonatrienone derivatives in moderate to good yields. In addition, the photophysical properties of the cycloadducts are presented.

Original languageEnglish
Pages (from-to)4757-4762
Number of pages6
JournalJournal of Organic Chemistry
Volume79
Issue number10
DOIs
StatePublished - 16 May 2014
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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