The Barbier-type propargylation of azo compounds with α,γ-disubstituted propargylic tosylates was achieved by using metallic barium as the promoter. Various propargylated hydrazines (α-adducts) were exclusively synthesized from the corresponding propargylic tosylates and azobenzenes (diaryldiazenes). The thus-obtained propargylic hydrazines were further efficiently converted into propargylic amines by reductive N–N bond cleavage. Benzidine rearrangement of the propargylic hydrazines was also attempted.

中文翻译：

---

使用金属钡选择性丙炔化二芳基偶氮化合物

以金属钡为促进剂，实现了偶氮化合物与 α,γ-二取代炔丙基甲苯磺酸酯的 Barbier 型炔丙基化反应。各种炔丙基化肼（α-加合物）完全由相应的炔丙基甲苯磺酸盐和偶氮苯（二芳基二氮烯）合成。由此获得的炔丙基肼通过还原性 N-N 键断裂进一步有效地转化为炔丙基胺。还尝试了炔丙基肼的联苯胺重排。