Ultrasound-enhanced reactivity of calcium in the reduction of aromatic hydrocarbons

Reductions of aromatic hydrocarbons by calcium in ethylenediamine-n-alkylamine mixture were investigated under ultrasonic conditions. Using an ultrasonic probe, with naphthalene as test molecule, it has been demonstrated that under ultrasonic action the reactions proceed faster (x10) and require a lower metal quantity (0.5) than the reactions conducted with an efficient mechanical stirrer. In addition, at ambient temperature and depending on the specific alcohol addition, selective naphthalene reduction can be performed using ultrasound. 1,2-Dihydronaphthalene (88% yield) results from the reaction in the presence of 2-propanol, and 1,4,5,8-tetrahydronaphthalene (88% yield) is obtained with tert-butanol. Investigation of the metal surface points out the characteristics of the calcium ultrasonic activation. The procedure was efficiently tested with several aromatic hydrocarbons. (C) 2000 Elsevier Science B.V. All rights reserved.