Hydrogen–deuterium exchange and rearrangement of polycyclic aromatic hydrocarbons in dilute acid medium at elevated temperatures

Abstract

The high temperature – dilute acid (HTDA) method has been applied to the preparation of perdeuterated polycyclic aromatic hydrocarbons. Naphthalene (1), 1-methylnaphthalene (2), 2-methylnaphthalene (3), anthracene (4), phenanthrene (5), chrysene (6), pyrene (7), benz[a]anthracene (8), benzo[a]pyrene (9), 1,1′-binaphthyl (10), 1,2′-binaphthyl (11), and 2,2′-binaphthyl (12) have been perdeuterated in high yield in dilute DCl–D2O solutions at elevated temperatures (240–280 °C). 2, 3, 10, 11, and 12 also rearrange.