Intramolecular [4 + 2] trapping of a hexadehydro-diels-alder (HDDA) benzyne by tethered arenes

Vedamayee D. Pogula, Tao Wang, Thomas R. Hoye

Research output: Contribution to journalArticlepeer-review

23 Scopus citations

Abstract

We report here the efficient, intramolecular trapping in a Diels-Alder (DA) sense of thermally generated benzynes by one of two pendant arene rings. A more electron-rich ring (p-methoxyphenyl) reacted substantially faster than a simple phenyl ring, which was, in turn, slightly more reactive vs a 4-carbomethoxyphenyl ring. Photoinduced di-π-methane rearrangement of the initial DA adducts gave rise to unusual isomeric polycyclic adducts.

Original languageEnglish (US)
Pages (from-to)856-859
Number of pages4
JournalOrganic Letters
Volume17
Issue number4
DOIs
StatePublished - Feb 20 2015

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