97513-16-1Relevant academic research and scientific papers
Investigations on Diazo Compounds and Azides, 58. Dication Ethers, 5. Formamidinium-substituted Diazaphosphoryl Compounds: Synthesis, Properties, and Reactions Leading to Tetrazoles
Maas, Gerhard,Guembel, Helmut,Weise, Gisela,Regitz, Manfred
, p. 2105 - 2117 (2007/10/02)
Electrophilic diazoalkane substitution of diazaphosphoryl compounds 4a-c by bis(formamidinium)ethers 3a, b leads to formamidinium-substitited (diazomethyl)phosphoryl compounds 5.These can also be considered as alkenediazonium salts, but the contribution from this resonance structure is low according to 1H NMR and IR data.Reaction of 5a-c with another equivalent of 4a-c under slightly modified conditions yields 2-vinyl-2H-tetrazoles 6 and 7.The identity of the tetrazoles has been confirmed by X-ray structure analysis of 6c as well as by thermolysis of 6c leading to pyrazole 12 which then was hydrolyzed to give the NH-pyrazole 13.
