Copper chloride with vinylic halides

Perfluoroalkynylcopper reagents can be prepared by metathesis reactions with the zinc or cadmium reagent (e.g., formation of 6) or by treatment of terminal (perfluoroalkyl)acetylenes with copper(I) chloride/ammonium hydroxide.69 Perfluoroalkynylcopper reagents react with aryl (e.g., formation of 7) and vinyl halides as well as undergoing oxidative dimerization reactions upon exposure to air.2... 

DIBAL-H/n-butyllithium, in cyclic and acyclic systems with iron pentacarbonyl, in cyclodecanes with lithium dihydrodimethoxyaluminate(III)/copper(I) iodide, and in cyclohexane and cyclopentane systems with NaH/sodium r-butylpentyl/Ni(OAc)2. ° The monoreduction of 1,3-diketones can be carried out under similar conditions, as illustrated by the reaction of a substituted cyclohexane-1,3-dione with oxalyl chloride to give the corresponding 1-chlorocyclohexenone, which was subsequently reduced to the enone with zinc-silver couple (Scheme 45). Kropp et al. have reported the photolytic reduction of vinyl iodides in acyclic systems however, when an a-hydrogen is present, formation of the diene product is a limiting side reaction (Scheme 46). For a more extensive discussion of vinyl halide reductions, see the preceding chapter in this volume. 

Copper(l) carboxylates give esters with primary (including neopentyl without rearrangement), secondary, and tertiary alkyl, allylic, and vinyhc halides7" A simple Sn mechanism is obviously precluded in this case. Vinylic halides can be converted to vinylic acetates by treatment with sodium acetate if palladium(ll) chloride... 

Irioxide, platinum, silver, potassium chlorate, potassium ferricyanide, potassium mercuric cyanide, silver chloride, stibine, tellurium halides, tellurium hydropentachloride, tetramethy-lammonium amide, trimethylammonium amide, trioxygen difluoride, vinyl acetate. Violent polymerization with ethylene oxide. Attacks some coatings, plastics, and rubber. Attacks copper, brass, bronze, aluminum, steel, and their alloys. 

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