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Arenesulfonamides, sulfamide, and cyanamide are efficiently allylated using allylic carbonates under Pd(0)-catalysis. N-Arenesulfonyl-2,5-dihydropyrroles are obtained by ruthenium-mediated ring closing metathesis of the corresponding N-diallylated compounds. A stereochemical study of the reactions of ethyl cis-(5-methyl-2-cyclohexenyl) carbonate with 2,4,6-triisopropylphenylsulfonamide was performed,...
Arenesulfonamides 10, cyanamide 29, and sulfamide 32 react with allylic bis-carbonates 8 (Z and E) and 9 under Pd(0)-catalysis to afford medium and large unsaturated heterocycles instead of three and/or five-membered ring compounds. Stable 15-membered palladium-containing rings were also isolated from arenesulfonamides and 8, with three trans olefinic systems coordinated to the metal. NMR and MALDI-TOF...
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