Copper (II) in organic synthesis. VI1 reaction of the copper (II) acetate complex of 1-methylisatin-3-chlorophenylhydrazone with dimethyl acetylenedicarboxylate

…, G Desimoni, AG Invernizzi, P Quadrelli, PP Righetti…

Index: Coda, Corsico A.; Desimoni, G.; Invernizzi, Gamba A.; Quadrelli, P.; Righetti, P. P.; Tacconi, G. Tetrahedron, 1987 , vol. 43, # 12 p. 2843 - 2852

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Citation Number: 2

Abstract

The copper (II) complex of 1-methylisatin-3-p-chlorophenyl hydrazone (2) reacted with dimethyl acetylenedicarboxylate (DMAD) in accordance to two reaction pathways. Oxidation performed by Cu++ gave 1-methyl-3-carbenindolin-2-one (12), trapped by DMAD to give products 3—5, and p-chlorophenylradical (13), trapped either by DMAD to give 6, or by the free ligand 1 to give 7 or by carbenindolinone and DMAD to give 8. The second pathway ...