| Abstract: | Contributions to the Chemistry of Hydrazine and its Derivatives. 53. Synthesis of P-, As-, and Sb-substituted Hydrazines by Addition of P? H, As? H, and Sb? H Groups to N?N Double Bonds Addition of diphenylphosphinous acid, diphenylthiophosphinous acid, methyl hydrogen phenylphosphonite, diethyl hydrogen phosphite, diphenylphosphane, dibutylphosphane, diphenylarsane, diethylarsane, and diphenylstibane to the N?N double bond of diethyl azodicarboxylate, dimethyl azodicarboxylate, ethyl phenylazocarboxylate, and azobenzene yields the P-, As-, and Sb- substituted hydrazines 1–23 . The spectroscopic data agree with the structural formulae. The course of the reactions suggests a polar reaction mechanism except in the case of the synthesis of 15 , which probably proceeds via radical intermediates. The azo systems employed show a distinct graduation in their ability to add to the element-hydrogen groups used. |
