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A reinvestigation of the reaction of 2,5-dmethylpyrazine in carbon tetrachloride solution with chlorine under ultraviolet light revealed that the product was Z-chloro-3,6-dimethylpyrazine (11) and that recourse to ultraviolet treatment was unnecessary. Treatment of 2-methylpyrazine with chlorine afforded a mixture of Zchloro-&methyl-(VII) and 5-chloro-5-methylpyrazine (VIII). In allon~ing 2,6-dimethylpyrazine to react, with chlorine, it was found that ultraviolet radiation was essential and that the product was an unstable side chain halogenated compound, 2,6-bis( a-chloromethy1)pyrazine (XV). Alcoholysis converted XV to the bis ether XVI. Treating 2-methyl-and 2,5-dimethylpyrazine with one equivalent of K-chlorosuccinimide and a small quantity of benzoyl peroxide afforded unstable or-chloromethyl derivatives V and X I which were converted to the corresponding side chain ethers VI and XII.