(Z)-1-Aryl-1-haloalkenes as intermediates in the Vilsmeier haloformylation of aryl ketones

Annamaria Lilienkampf; Mikael P Johansson; Kristiina Wähälä

doi:10.1021/ol034914c

(Z)-1-Aryl-1-haloalkenes as intermediates in the Vilsmeier haloformylation of aryl ketones

Org Lett. 2003 Sep 18;5(19):3387-90. doi: 10.1021/ol034914c.

Authors

Annamaria Lilienkampf¹, Mikael P Johansson, Kristiina Wähälä

Affiliation

¹ Department of Chemistry, Laboratory of Organic Chemistry and Laboratory for Instruction in Swedish, University of Helsinki, P.O. Box 55, FIN-00014, Finland.

PMID: 12967281
DOI: 10.1021/ol034914c

Abstract

[reaction: see text] Vilsmeier reagents give (Z)-1-aryl-1-haloalkenes from aryl ketones bearing an electron-donating substituent at the ortho- or para-position. These haloalkenes are intermediates in the Vilsmeier haloformylation of the aryl ketones. Another reaction mechanistic pathway is thus available in certain Vilsmeier haloformylations, in competition with the commonly accepted route by way of an enaminoketone.