Diels-Alder reaction of tropones with arynes: synthesis of functionalized benzobicyclo[3.2.2]nonatrienones.
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.
Organic Chemistry Division, ‡Physical and Materials Chemistry Division, and §Center for Materials Characterization, CSIR-National Chemical Laboratory (CSIR-NCL) , Dr. Homi Bhabha Road, Pune 411008, India.
Manikandan
M
Thangaraj
Sachin Suresh
SS
Bhojgude
Rajesh H
RH
Bisht
Rajesh G
RG
Gonnade
Akkattu T
AT
Biju