6533b853fe1ef96bd12ad687

RESEARCH PRODUCT

Unexpected Formation of a 1,2-Dichloroacenaphthylene in a Friedel-Crafts Reaction with Chloral Hydrate

Till OpatzDieter SchollmeyerSonja Schwolow

subject

ChemistryElectrophileChloral hydrateX-ray crystallographymedicineGeneral ChemistryMedicinal chemistryFriedel–Crafts reactionmedicine.drug

description

An unprecedented rearrangement was encountered during an attempted alkylation of an electron-rich naphthalene with chloral hydrate. The reaction produced a dichlorinated acenaphthylene and presumably involves the intermediate formation of a chloronium ion which is opened to produce the five-membered ring of the final product.

https://doi.org/10.5560/znb.2012.67b0272