108726-06-3Relevant articles and documents
The reaction of cyclohexanone azine with PCl3. synthesis of annulated dichlorodiazaphosphole and its unusual transannulation
Kornev, Alexander N.,Gorak, Olga Y.,Lukoyanova, Olga V.,Sushev, Vyacheslav V.,Panova, Julia S.,Baranov, Evgenii V.,Fukin, Georgy K.,Ketkov, Sergei Y.,Abakumov, Gleb A.
experimental part, p. 1173 - 1178 (2012/08/28)
The N, N'-annulated dichlorodiazaphosphole 1 was prepared in 55€‰% yield by the reaction of cyclohexanone azine (c-HA) with two equivalents of PCl3 in pyridine. Compound 1 revealed one-dimensional chains in crystal with short intermolecular interactions [3.194(1) A] between phosphorus atoms of adjacent molecules. Treatment of c-HA with MeLi (2 equiv. in Et2O) followed by addition of PCl3 gave 1 in 33€‰% yield. An amount of c-HA isomerizes in these conditions to form corresponding hexahydroindazole derivative 3, which further reacts with 1 to give diazaphosphole 5 as transannulation product. Copper monochloride forms an (1:1) adduct with 5, which was characterized by its X-ray crystal structure. Only one equivalent of PCl3 reacts with c-HA in Et 2O/Et3N mixture to form diazaphospholium chloride 2 and hexahydroindazole 3.
