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• W1997357108 abstract "The facile activation of cis- and trans-1,2-diphenylbenzocyclobutene (DBC) either by charge-transfer irradiation of the electron donor-acceptor complex with tetracyanoethylene or by chloranil photosensitization leads to a series of rapid [4 + 2] cycloadditions. The role of the cation radical DBC+. as the reactive intermediate which undergoes a stereospecific, conrotatory cycloreversion is delineated, especially with regard to “contact” and “solvent-separated” ion pairs. Such cycloadditions induced by electron transfer are discussed in the context of the thermal valence tautomerization of DBC previously established by Huisgen, Quinkert, and co-workers. Elektron-Transfer-Photochemie von Benzocyclobutenen. – Stereospezifische elektrocyclische Reaktionen ihrer Kation-Radikale Die leichte Aktivierung von cis- und trans-1,2-Diphenylbenzocyclobuten (DBC) entweder durch Bestrahlung der Charge-transfer-Verbindung mit Tetracyanethylen oder durch Photosensibilisierung mit Chloranil führt zu einer Serie schneller [4 + 2]-Cycloadditionen. Die Rolle des Kationradikals DBC+. als reaktives Zwischenprodukt, das eine stereospezifische conrotatorische Cycloreversion eingeht, wird vorwiegend über „Kontakt”︁- oder „Lösungsmittel-getrennte”︁ Ionen-Paare erklärt. Solche Cycloadditionen, die durch einen Elektronentransfer eingeleitet werden, werden im Zusammenhang mit einer thermischen Valenztautomerie von DBC diskutiert, wie sie früher von Huisgen, Quinkert und Mitarbeitern begründet wurden." @default.
• W1997357108 created "2016-06-24" @default.
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• W1997357108 date "1988-02-01" @default.
• W1997357108 modified "2023-10-11" @default.
• W1997357108 title "Electron‐transfer photochemistry of benzocyclobutenes stereospecific electrocyclic reactions of their cation radicals" @default.
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• W1997357108 doi "https://doi.org/10.1002/cber.19881210210" @default.
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