Sven Mangelinckx, M. Boeykens, N. Kimpe
May 1, 2008
Citations
0
Influential Citations
2
Citations
Journal
Synlett
Abstract
2-(Dichloromethylene)azetidines constitute a new class of stable exocyclic enamines. The synthesis of these inductively stabilized N-alkyl-2-methyleneazetidines entails the imination of β-halo ketones, followed by α′,α′-dichlorination and subsequent 1,4-dehydrohalogenation. The synthesis of these azetidines is easy and can be performed on multigram scale in good yield. 2-(Dichloro-methylene)azetidines undergo smooth reactions towards electrophilic reagents as evidenced by the ready alkoxyhalogenation and hydrolysis to pyrrolidin-3-ones.