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COMPARATIVE CHEMICAL STUDIES OF THE BEHAVIOR OF 4-CYANO-1,2-DITHIOLES IN ANALOGY WITH 1,2,4-DITHIAZOLES TOWARD STABLE PHOSPHONIUM YLIDES
Abdou, Wafaa M.,Ganoub, Neven A. F.
, p. 63 - 72 (2007/10/03)
The reaction of 5-p-chlorophenyl-4-cyano-1,2-dithiole-3-thione 2a or its 3-carbonyl derivative 2b with phosphonium ylides 1a and 1b afforded, in both cases, compounds 10a,b and 13a,b.In addition, compound 11a or 11b was also isolated from the first reaction (2a + 1a,b).Reaction of 1c with 2a as with 2b afforded compounds 10c and 14.The transformations 10a and 11a 13a as well as 10c 14 were also studied.Reaction of 2a with fluorenylidenetriphenylphosphorane 1d afforded, besides the expected olefin 10d, the dithione 15, while 2b with 1d yielded 10d and theknown ethylene compound 4.Reduction of 15 by Cu powder yielded 4.When the reactions of 2a or 2b with 1a-c were performed in the presence of triethylamine, both the expected products 10a-c and 22a-c were obtained.The addition of triethylamine to the reaction mixture of 2a or 2b with 1d did not affect the result.Key words: 5-p-Chlorophenyl-4-cyano-1,2-dithioles, heterocyclic-cis-disulfides, phosphonium ylides, Wittig reaction.
