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Intramolecular [4 + 2] trapping of a hexadehydro-Diels-Alder (HDDA) benzyne by tethered arenes.

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-?-methane rearrangement of the initial DA adducts gave rise to unusual isomeric polycyclic adducts.

SUBMITTER: Pogula VD

PROVIDER: S-EPMC4729866 | biostudies-literature | 2015 Feb

REPOSITORIES: biostudies-literature

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Intramolecular [4 + 2] trapping of a hexadehydro-Diels-Alder (HDDA) benzyne by tethered arenes.

Pogula Vedamayee D VD Wang Tao T Hoye Thomas R TR

Organic letters 20150211 4

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. ...[more]

PMID: 25671804

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