1172610-31-9Relevant academic research and scientific papers
Mesoionic 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
Araki, Shuki,Yokoi, Keisaku,Sato, Ryosuke,Hirashita, Tsunehisa,Setsune, Jun-Ichiro
, p. 164 - 171 (2009)
The reactions of 1, 3-diphenyltetrazol-5-ylidene, a rare example of mesoionic carbenes, with electron- deficient 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 mono- and 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.
