Palladium catalyzed oxidation of monoterpenes:: novel oxidation of myrcene with dioxygen

Myrcene can be efficiently and selectively oxidized by dioxygen in glacial acetic acid containing LiCl, in the presence of the PdC2-CuCl2 catalytic combination, yielding two isomers of a new functionalized monoterpene, i.e., 3-(1-acetoxy-1-methylethyl)-1-vinylcyclopentene and 4-(1-acetoxy-1-methylethyl)-1-vinylcyclopentene, as major products. These compounds have a pleasant scent with a flower or fruit tinge and could be used as components of synthetic perfumes. The activities of Pd(OAc)(2)-LiNO3, Pd(OAc)(2)-Cu(NO3)(2) and Pd(OAc)(2)-benzoquinone systems in myrcene oxidation have also been examined. (C) 2002 Elsevier Science B.V. All rights reserved.