Diels-alder reaction of tropones with arynes: synthesis of functionalized benzobicyclo[3.2.2]nonatrienones

TitleDiels-alder reaction of tropones with arynes: synthesis of functionalized benzobicyclo[3.2.2]nonatrienones
Publication TypeJournal Article
Year of Publication2014
AuthorsThangaraj, M, Bhojgude, SSuresh, Bisht, RH, Gonnade, RG, Biju, AT
JournalJournal of Organic Chemistry
Volume79
Issue10
Pagination4757–4762
Date PublishedAPR
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.

DOI10.1021/jo500819w
Funding Agency

Council of Scientific & Industrial Research (CSIR) - India

Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

4.785

Divison category: 
Center for Material Characterization (CMC)
Organic Chemistry
Physical and Materials Chemistry