Thiyl Radical Mediated Racemization of Nonactivated Aliphatic Amines
The Journal of Organic Chemistry2006Vol. 71(19), pp. 7288–7292
Citations Over TimeTop 18% of 2006 papers
Stéphanie Escoubet, Stéphane Gastaldi, Nicolas Vanthuyne, Gérard Gil, Didier Siri, Michèle P. Bertrand
Abstract
The racemization of nonactivated aliphatic amines has been mediated with alkanethiols and with methyl thioglycolate in the presence of AIBN. The process involves reversible H-abstraction at the chiral center, in a position alpha relative to nitrogen, by thiyl radical. The knowledge of the reaction enthalpy is critical to select the appropriate thiol. In the absence of experimental values, theoretical calculations of the alpha-C-H BDEs and the S-H BDE provide a useful guide.
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