Browsing by Subject "Walsh Orbital"

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    Lewis Acid-mediated Formation of 1,3-Disubstituted Spiro[cyclopropane-1,2'-indanes]: The Activating Effect of the Cyclopropane Walsh Orbital
    (American Chemistry Society, 2020-02) Alajarín, Mateo; Ballester, Francisco-Jose; Vivancos, Juan-Antonio; Orenes, Raul-Angel; Vidal, Angel; Sanchez-Andrada, Pilar; Marin-Luna, Marta; Química Orgánica
    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.