in Wiley InterScience (www.interscience.wiley.com).The reactions of 1,3-diphenyltetrazol-5-ylidene, a rare example of mesoionic carbenes, with electrondeficient unsaturated compounds were studied. The carbene reacted with dimethyl 1,2,4,5-tetrazine-3, 6-dicarboxylate to give a 5-tetrazoliomethylide, together with hydrazine derivatives. The reaction with tetracyanoethylene gave another methylide in low yield. On the contrary, the reactions with weaker electrophiles, such as 3,6-diphenyl-1,2,4,5-tetrazine, fumalonitrile, N-phenylmaleimide, and dimethyl acetylenedicarboxylate, did not give any coupling products, but gave phenylated products and/or Michael addition products via the degradation of the 1,3-diphenyltetrazole ring. Novel mesoionic monoand bis(carbene)-rhodium(I) complexes were synthesized and the structures were characterized by X-ray crystallography. Their catalytic activities for the decarbonylative addition reaction of benzoyl chloride to ethynylbenzene were investigated.
Polyphenylalkene derivatives Q 0740Mesoionic Carbenes: Reactions of 1,3-Diphenyltetrazol-5-ylidene with Electron--Deficient Alkenes and Synthesis and Catalytic Activities of the (Tetrazol--5-ylidene)rhodium(I) Complexes. -Novel mesoionic carbenes are synthesized and their catalytic activity for the decarbonylative addition reaction of benzoyl chloride (II) to ethynylbenzene (I) is investigated. -(ARAKI*, S.; YOKOI, K.; SATO, R.; HIRASHITA, T.; SETSUNE, J.-I.; J. Heterocycl. Chem. 46 (2009) 2, 164-171; Grad. Sch. Eng., Omohi Coll., Nagoya Inst. Technol., Showa, Nagoya 466, Japan; Eng.) -M. Paetzel 36-088
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