Lewis Acid-Mediated Formation of 1,3-Disubstituted Spiro[cyclopropane-1,2'-indanes]: The Activating Effect of the
Mateo Alajarin1, Francisco-Jose Ballester1, Juan-Antonio Vivancos1
1Departamento de Quı́mica Orgánica, Facultad de Quı́mica, Regional Campus of International Excellence "Campus Mare Nostrum", Universidad de Murcia, Murcia 30100, Spain.
Abstract:
By virtue of its alkylidenecyclopropane moiety, 2-(cyclopropylidenemethyl)benzaldehyde reacts with a range of amines and thiols under Lewis acid catalysis. These reactions yield 1,3-bis(arylamino) and 1,3-bis(arylthio and alkylthio)indanes, respectively, which are spirolinked to the cyclopropane ring at carbon 2. The reaction mechanism, and the peculiar contribution of the cyclopropane ring, have been scrutinized via DFT calculations.
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