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

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

doi:10.1021/ol5037024

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 journal › Article › peer-review

32 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 language	English (US)
Pages (from-to)	856-859
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	4
DOIs	https://doi.org/10.1021/ol5037024
State	Published - Feb 20 2015

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© 2015 American Chemical Society.

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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.",

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AU - Wang, Tao

AU - Hoye, Thomas R.

PY - 2015/2/20

Y1 - 2015/2/20

N2 - 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.

AB - 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.

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

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