ChemInform Abstract: Reactivity of 4,5‐Tetramethylene‐2‐cyclohexyl‐1,2,3‐diazaphosphole.

Abstract

Methanol (II) attacks the title compounds at the P=C bond to give the adduct (III) which is transformed during distillation into the hydrazone (IV).

Cycloaddition reactions of heterophospholes

“…Similar reactions are given by AlCl 3 -complexed 1-phenyl-1,3,2-benzodiazaphosphole [87] and 1,3,2-benzoxazaphosphole [18] with ␣-diimines. A cyclohexane anellated 1,2,3-diazaphosphole reacts analogously [79].…”

“…Cyclohexane-anellated 1,2,3-diazaphosphole forms unstable cycloadducts with diazoalkanes which eliminate nitrogen to form mixtures of acyclic bis(hydrazones) and 3 P compounds [79]. The cycloadduct of 1,2,3-diazaphospholes with phenyl azide splits off nitrogen to generate phosphinimine which trimerizes [80].…”

Anellated Heterophospholes and Phospholides and Analogies with Related Non-Phosphorus Systems

“…The reaction with ethylene glycol leads to a spirocyclic σ 5 P product 150 through 1,2-addition followed by the 1,1-addition of the other hydroxy group (Scheme ) 59c. A cyclohexane-anellated 1,2,3-diazaphosphole is reported to undergo 1,2-addition with MeOH, but as the product is unstable it loses phosphorus to form a hydrazone 51 …”

“…1,3-Dipolar cycloadditions of diazoalkanes on a cyclohexane-anellated 1,2,3-diazaphosphole have been reported. The products are, however, unstable and lose nitrogen to form a mixture of acyclic bis(hydrazones) and σ 3 P compounds …”

“…The reactions of a cyclohexane-anellated 1,2,3-diazaphosphole with cyclohexanone and phenyl azide leading to 1,1-additions on phosphorus have been reported …”