Heterocyclic and acyclic derivatives of -N-isopropylacetimidoyl chloride |
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Authors: | Keith E Peterman Jeanne M Shreeve |
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Institution: | Department of Chemistry, University of Idaho, Moscow, Idaho 83843 USA |
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Abstract: | -N-Isopropylacetimidoyl chloride, CF3CClNCF(CF3)2, has been used as a precursor for a variety of heterocyclic and acyclic compounds. Reaction with azide ion yields a mixture of the imidoyl azide, CF3(N3)CNCF(CF3)2, and the 1,5-tetrazole, CF3CF(CF3)2. Hexafluoropropylideniminolithium produces as a minor product the conjugated diimine, (CF3)2CNC(CF3)NCF(CF3)2, from nucleophilic attack at the imidoyl chlorine and as a major product the triimine, (CF3)2CNC(CF3)NC(CF3)2NC(CF3)2, from further attack at the isopropyl fluorine. A thio-amide, CF3C(S)NHCH(CF3)2, and a Δ3-1,2,4-dithiazoline, (CF3)2, are produced upon reaction of hyrogen sulfide with the imidoyl chloride. Pathways are proposed for each of the reactions. |
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