Small-Ring Compounds. XXVI. Nucleophilic Displacement Reactions of Some Halogen-substituted Phenylcyclobutenones

Abstract

Displacement reactions between alkali hxlides and several cyclic allylic-type halides, namely, 2,2-dihalo-3-phenylcyclo,-butenones, have been found to proceed with rearrangement to give 2,4-dihalo-3-phenylcyclobutenones. The 2,2-dihalocompounds also were found to rearrange to the corresponding allylic isomers on heating with triethylamine. The allylic iodides, 2-fluoro-4-iodo- and 2-chloro-4-iodo-3-plienyl-2-cyclobutenones,rearranged in reactions with halogens to form 2,2-dihalo-3-phenylcyclobutenones. Evidence is presented for the stereospecific nature of these reactions