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Dejaegher Y, Mangelinckx S, De Kimpe N. Rearrangement of 2-aryl-3,3-dichloroazetidines: intermediacy of 2-azetines. J Org Chem. 2002;67(7):2075-81doi: 10.1021/jo010914j.
Dejaegher, Y., Mangelinckx, S., & De Kimpe, N. (2002). Rearrangement of 2-aryl-3,3-dichloroazetidines: intermediacy of 2-azetines. The Journal of organic chemistry, 67(7), 2075-81. https://doi.org/10.1021/jo010914j
Dejaegher, Yves, et al. "Rearrangement of 2-aryl-3,3-dichloroazetidines: intermediacy of 2-azetines." The Journal of organic chemistry vol. 67,7 (2002): 2075-81. doi: https://doi.org/10.1021/jo010914j
Dejaegher Y, Mangelinckx S, De Kimpe N. Rearrangement of 2-aryl-3,3-dichloroazetidines: intermediacy of 2-azetines. J Org Chem. 2002 Apr 05;67(7):2075-81. doi: 10.1021/jo010914j. PMID: 11925211.
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J Org Chem. 2002 Apr 05;67(7):2075-81. doi: 10.1021/jo010914j.

Rearrangement of 2-aryl-3,3-dichloroazetidines: intermediacy of 2-azetines.

The Journal of organic chemistry

Yves Dejaegher, Sven Mangelinckx, Norbert De Kimpe

Affiliations

  1. Department of Organic Chemistry, Faculty of Agricultural and Applied Biological Sciences, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium.

PMID: 11925211 DOI: 10.1021/jo010914j

Abstract

An easy synthesis of 2-aryl-3,3-dichloroazetidines, a rather unexplored class of azaheterocycles, is described. The title compounds were easily obtained by reduction of the corresponding 4-aryl-3,3-dichloro-2-azetidinones with monochloroalane, which in turn were synthesized by a ketene-imine [2 + 2] cycloaddition. The reactivity of 3,3-dichloroazetidines with bases was investigated, yielding 2-[dimethoxy(aryl)methyl]aziridines by ring contraction when treated with sodium methoxide. Furthermore, reacting the 3,3-dichloroazetidines with sodium hydride in DMSO, followed by aqueous workup, afforded 1-alkyl-2-aroylaziridines, by hydrolysis of the intermediate 2-azetines and ring closure of the transient 3-amino-2-chloro-1-phenyl-1-propanone derivatives. Monitoring this reaction in an NMR tube, using sodium hydride in DMSO-d(6), allowed the characterization of the intermediate strained heterocyclic enamines, i.e., 2-azetines, by (1)H and (13)C NMR.

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