Diels–Alder Reaction of Tropones with Arynes: Synthesis of Functionalized Benzobicyclo[3.2.2]nonatrienones

Thangaraj, Manikandan ; Bhojgude, Sachin Suresh ; Bisht, Rajesh H. ; Gonnade, Rajesh G. ; Biju, Akkattu T. (2014) Diels–Alder Reaction of Tropones with Arynes: Synthesis of Functionalized Benzobicyclo[3.2.2]nonatrienones The Journal of Organic Chemistry, 79 (10). pp. 4757-4762. ISSN 0022-3263

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Official URL: http://doi.org/10.1021/jo500819w

Related URL: http://dx.doi.org/10.1021/jo500819w

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.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society
ID Code:128687
Deposited On:03 Nov 2022 06:53
Last Modified:03 Nov 2022 06:53

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