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Updated: May 4, 2026

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
Published on: April 19, 2019
Gold(I) carbenes by retro-Buchner reaction: generation and fate
Yahui Wang1, Paul R McGonigal, Bart Herlé
1Institute of Chemical Research of Catalonia (ICIQ) , Av. Paísos Catalans 16, 43007 Tarragona, Spain.
Abstract:
The fate of the aryl gold(I) carbenes generated by retro-Buchner reaction of ortho-substituted 7-aryl-1,3,5-cycloheptatrienes is dependent on the constitution of the ortho substituent. Indenes and fluorenes are obtained by intramolecular reaction of highly electrophilic gold(I) carbenes with alkenes and arenes. According to density functional theory calculations, the gold-catalyzed retro-Buchner process occurs stepwise, although the two carbon-carbon cleavages occur on a rather flat potential energy surface.
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