Substitution of acetylenic groups for halogen in the quinonoid ring

The bromine or iodine atom in the quinonoid ring devoid of +M substituent in the position neighboring to the halogen is replaced by acetylenic groups on treatment with Cu^I acetylides, prepared either beforehand or in situ, in a mixture of DMSO and CHCl₃ in the presence of a Pd complex catalyst. A series of mono- and diacetylenic derivatives of 1,4-naphtho- and 1,4-benzoquinone were prepared. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1636–1639, July, 2005.