Abstract: The sexual attractant of the gypsy moth, cis-7,8-epoxy-2-methyloctadecane, is prepared by reacting isoheptyl bromide with an organometallic compound of dodecine-(1) in the presence of an anhydrous polar organic diluent at a temperature of about 20.degree. to 150.degree.C to produce 2-methyloctadecine-(7),hydrogenating the 2-methyloctadecine-(7) in the presence of a palladium catalyst and at a temperature of about -10.degree. to +60.degree.C in a diluent to produce 2-methyloctadecene-7-cis and epoxidizing the 2-methyloctadecene-7-cis to produce cis-7,8-epoxy-2-methyloctadecane. The organometallic compound of dodecine-1 is prepared by reaction of dodecine-1 with lithium, sodium or potassium amide freshly prepared in liquid ammonia or a solution of alkyl-lithium.

Abstract: Compounds of the formulaR.sup.1 --C.tbd.C--R.sup.2 (I)whereinR.sup.1 is hydrogen, unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted polyalkenyl, or unsubstituted or substituted polyalkynyl, andR.sup.2 is unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted polyalkenyl or unsubstituted or substituted polyalkynyl,Are produced by reacting a compound of the formulaR.sup.1 --C.tbd.CH (II)whereinR.sup.1 is as above defined in a mixture comprising a copper(I) halide or copper(I) cyanide, a bicyclic amidine base and a catalytic amount of an antioxidant or mixture of antioxidants, in an organic solvent or mixture of solvents, at a temperature of from -40.degree. C to +100.degree. C, with a compound of the formulaX--R.sup.2 (III)whereinX is halogen, andR.sup.2 is as above defined.