Publication: Lewis Acid-mediated Formation of 1,3-Disubstituted Spiro[cyclopropane-1,2'-indanes]: The Activating Effect of the Cyclopropane Walsh Orbital
Authors
Alajarín, Mateo ; Ballester, Francisco-Jose ; Vivancos, Juan-Antonio ; Orenes, Raul-Angel ; Vidal, Angel ; Sanchez-Andrada, Pilar ; Marin-Luna, Marta
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Publisher
American Chemistry Society
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DOI
10.1021/acs.joc.0c00090
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info:eu-repo/semantics/article
Description
Abstract
By virtue of its alkylidenecyclopropane moiety 2-(cyclopropylidenemethyl)benzaldehyde reacts with a range of amines or thiols under Lewis acid catalysis yielding the respective 1,3-bis(arylamino) or -bis(arylthio and alkylthio)indanes spirolinked to the cyclopropane ring at carbon 2. The reaction mechanism and the peculiar contribution of the cyclopropane ring have been scrutinized by DFT calculations.
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Citation
J. Org. Chem. 2020, 85, 6, 4565–4573
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