Synthesis, Structure and Reactivity of a Cyapho(dicyano)methanide Salt.

ABSTRACT: We describe the synthesis of a cyapho(dicyano)methanide salt, [K(18-crown-6)][C(CN)₂ (CP)], from reaction of [Na(18-crown-6)][PH₂ ] (18-crown-6=1,4,7,10,13,16-hexaoxacyclooctadecane) with 1,1-diethoxy-2,2-dicyanoethylene (EtO)₂ C=C(CN)₂ . The reaction proceeds through a Michael addition-elimination pathway to afford [Na(18-crown-6)][HP{C(OEt)=C(CN)₂ }]. Addition of a strong, non-nucleophilic base (KHMDS) to this intermediate results in the formation of [K(18-crown-6)][C(CN)₂ (CP)]. Subsequent reactivity studies reveal that the cyapho(dicyano)methanide ion is susceptible to protonation with strong acids to afford the parent acid HC(CN)₂ (CP). The reactivity of the cyaphide moiety in [C(CN)₂ (CP)]^-</

SUBMITTER: Hu C 

PROVIDER: S-EPMC9805078 | biostudies-literature | 2022 Sep

REPOSITORIES: biostudies-literature