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Benzocyclobutadienes: An Unusual Mode of Access Reveals Unusual Modes of Reactivity.


ABSTRACT: The reaction of an aryne with an alkyne to generate a benzocyclobutadiene (BCB) intermediate is rare. We report here examples of this reaction, revealed by Diels-Alder trapping of the BCB by either pendant or external electron-deficient alkynes. Mechanistic delineation of the reaction course is supported by DFT calculations. A three-component process joining the benzyne first with an electron-rich and then with an electron-poor alkyne was uncovered. Reactions in which the BCB functions in a rarely observed role as a 4??diene component in Diels-Alder reactions are reported. The results also shed new light on aspects of the hexadehydro-Diels-Alder reaction used to generate the benzynes.

SUBMITTER: Xiao X 

PROVIDER: S-EPMC6296485 | biostudies-literature | 2018 Jul

REPOSITORIES: biostudies-literature

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Benzocyclobutadienes: An Unusual Mode of Access Reveals Unusual Modes of Reactivity.

Xiao Xiao X   Woods Brian P BP   Xiu Wen W   Hoye Thomas R TR  

Angewandte Chemie (International ed. in English) 20180704 31


The reaction of an aryne with an alkyne to generate a benzocyclobutadiene (BCB) intermediate is rare. We report here examples of this reaction, revealed by Diels-Alder trapping of the BCB by either pendant or external electron-deficient alkynes. Mechanistic delineation of the reaction course is supported by DFT calculations. A three-component process joining the benzyne first with an electron-rich and then with an electron-poor alkyne was uncovered. Reactions in which the BCB functions in a rare  ...[more]

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