Reactions of epoxy‐1,1,2‐trichloroethane with nudeophiles | Zendy

Kline Stanley A. | Zendy; Van Duuren Benjamin L. | Zendy

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

Author(s) -

Kline Stanley A.,

Van Duuren Benjamin L.

Publication year - 1977

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.5570140320

Subject(s) - chemistry , epoxy , thio , hydrolysis , trichloroethylene , silica gel , base (topology) , medicinal chemistry , organic chemistry , polymer chemistry , nuclear chemistry , mathematical analysis , mathematics

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 ).

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