The Friedel-Crafts reaction of acid chlorides with ethene; di-addition and molecular rearrangement

Article abstract of DOI:10.1016/S0040-4020(01)80962-5

Acid chlorides, complexed with excess aluminium chloride, reacted with ethene to form 3-methyl-2-buten-1-ones, i.e. rearranged di-addition products having a terminal isoprenoid skeleton, together with the usual β-chloropropanones. The latter were the sole products in the absence of excess catalyst. Acid chlorides containing a suitably situated π-system underwent intramolecular cyclization, e.g. 2-phenylcyclopropanecarbonyl chloride (10) cyclized to 3,4-benzobicyclo[3.1.0]hexan-2-one (11).