Reactions of epoxy-1,1,2-trichloroethane with nudeophiles

Epoxy-1,1,2-triehloroethane (1) was synthesized by the autuoxidation of trichloroethylene and was characterized. It was shown to react readily with 2-mercaptobenzirnidazole (2), 1 -melhyl-2-mercaptoimidazole ( 3 ), p-nitrolhiophenol ( 4 ), and 3,4-dichlorolhiophenol ( 5 ) forming 2-chloro-2-(benzirnidazole-2-thio)acelie acid ( 6 ), 2-ehloro-2-(1-methylirnidazole-2-thio)aeetic acid (characterized as methyl ester ( 8 )), 2-chloro-2-(4-nitrolhiothiophenoxy)-4-nilrophenylthioaeetate (9), and 2-chloro-2-(3,4-dichlorothiophenoxy)-3,4-dichlorophenylthioaeetale ( 10 ), respectively. Base hydrolysis of 9 yielded 2,2-di(4-nilrothiophenoxy)acetie acid ( 11 ). Adducl 9 decomposed on silica gel yielding p-nitrophcnyldisulfide ( 12 ).