1070-3632/04/7404-0578 2004 MAIK Nauka/Interperiodica Russian Journal of General Chemistry, Vol. 74, No. 4, 2004, pp. 578 581. Translated from Zhurnal Obshchei Khimii, Vol. 74, No. 4, 2004, pp. 633 636. Original Russian Text Copyright 2004 by Dikusar, Potkin, Vashkevich, Kozlov, Kaberdin. Synthesis and Properties of Copper, Mercury, and Silver (2-Naphthyl)acetylenides E. A. Dikusar, V. I. Potkin, E. V. Vashkevich, N. G. Kozlov, and R. V. Kaberdin Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus, Minsk, Belarus Received October 22, 2002 Abstract (Z)-2-Naphthylacetylene was synthesized by the reaction of (Z)-3-(2-naphthyl)-3-chloropropenal (prepared from 2-acetylnaphthalene) with aqueous NaOH in dioxane. The reactions of 2-naphthylacetylene with CuCl, [Ag(NH 3 ) 2 ]NO 3 , and K 2 [HgI 4 ] gave copper, silver, and mercury 2-naphthylacetylenides, respec- tively. Silver naphthylacetylenide reacts with iodine to give the iodoethynyl derivative, which readily takes up bromine across the triple bond. Naphthalene derivatives are widely used in syn- thesis of dyes, pesticides, and drugs [1, 2]. One of convenient routes to naphthalene functional deriva- tives is introduction of the ethynyl group into the side chain of the naphthalene system [3], followed by syn- thesis of highly reactive metal acetylenides [4, 5]. The goal of this work was synthesis of copper, mercury, and silver 2-naphthylacetylenides from ac- cessible 2-acetylnaphthalene I. First, we prepared (Z)-3-(2-naphthyl)-3-chloropropenal II by Vilsmeier Haack formylation of ketone I. We were able to iso- late and identify the intermediate reaction product, 3-(2-naphthyl)-3-chloro-2-propen-1-yl-N,N-dimethyl- immonium chloride III (yield 90%), whose treatment with sodium acetate in aqueous solution gave naph- thylchloropropenal II in 72% yield (see scheme below). Me O PCl 5 /HC(O)NMe 2 N ( C H 3 ) 2 + Cl dioxane Cl O I III AcONa, H 2 O IV II Cu Ag Hg 2 K 2 [HgI 4 ] [Ag(NH 3 ) 2 ]NO 3 CuCl V VI VII I 2 , CHCl 3 I Br 2 , CH 2 Cl 2 Br < > > < < > > < Br I VIII IX aqueous NaOH Cl