Synthesis, structure and reactivity of a cyapho-cyanamide salt
<p>We describe a facile synthesis of the cyapho-cyanamide salt [Na(18-crown-6)][N(CN)(CP)] from reaction of [Na(18-crown-6)][PH<sub>2</sub>] (18-crown-6=1,4,7,10,13,16-hexaoxacyclooctadecane) with dimethyl <em>N</em>-cyanocarbonimidate, (MeO)<sub>2</su...
| Main Authors: | , |
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| Format: | Journal article |
| Language: | English |
| Published: |
Wiley
2021
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| Summary: | <p>We describe a facile synthesis of the cyapho-cyanamide salt [Na(18-crown-6)][N(CN)(CP)] from reaction of [Na(18-crown-6)][PH<sub>2</sub>] (18-crown-6=1,4,7,10,13,16-hexaoxacyclooctadecane) with dimethyl <em>N</em>-cyanocarbonimidate, (MeO)<sub>2</sub>C=N(CN). The reaction proceeds with elimination of two equivalents of methanol. Careful tuning of the reaction conditions allowed for the isolation and characterization of the <em>N</em>-cyano(carboximidate)phosphide intermediate [HP{C(OMe)N(CN)}]<sup>−</sup>. Due to the adverse effects of methanol in these reaction mixtures, a bulk scale synthesis of [Na(18-crown-6)][N(CN)(CP)] could be achieved by addition of a base (LiHMDS) to neutralize the resulting alcohol. Further reactivity studies of this anion reveal that functionalization at the phosphorus atom is viable to yield a new family of cyanide-functionalised phosphorus heterocycles.</p> |
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