Oxidative coupling of acetylene compound with cupric salt in the solid state was found to proceed efficiently and selectively. The coupling reaction of α,ω-diacetylenes in the solid state gave the linear oligomers in contrast with the formation of the cyclic products in the solution reaction.

A novel access to 3-hydroxycephems was attained from penicillin G via the C=C bond cleavage of 1-(1-alkoxycarbonyl-2-chloromethyl-2-propenyl)-4-(phenylsulfonylthio)-2-azetidinones by successive treatment with RuCl3/HIO4 and HIO4/CuSO4 and reductive cyclization of 1-(1-alkoxycarbonyl-3-chloro-2-hydroxy-1-propenyl)-4-(phenylsulfonylthio)-2-azetidinones on treatment with a newly devised BiCl3/Sn or TiCl4/Sn bimetal redox couple in DMF containing pyridine.

No abstract

Electrolysis of 3-arylthiomethyl-D 3 -cephems possessing various substituents on the arylthio moiety undergo chemoselective and product-selective electrooxidation to give several different products. These include isomeric mixtures of the corresponding methoxylated cephems, a bis[(D 3 -cephem-3-yl)methyl]disulfide or a 3-dimethoxymethyl-D 3 -cephem. The selectivity of the oxidation is highly dependent on the nature of the substituents on the arylthio moiety which suggests that both steric and electronic effects play an important role in the electrooxidation of 3-arylthiomethyl-D 3 -cephems.

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