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...
| मुख्य लेखकों: | , |
|---|---|
| स्वरूप: | Journal article |
| भाषा: | English |
| प्रकाशित: |
Wiley
2021
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| _version_ | 1826308539515142144 |
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| author | Ergöçmen, D Goicoechea, JM |
| author_facet | Ergöçmen, D Goicoechea, JM |
| author_sort | Ergöçmen, D |
| collection | OXFORD |
| description | <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> |
| first_indexed | 2024-03-07T07:22:07Z |
| format | Journal article |
| id | oxford-uuid:2b97ea55-fc9f-49fc-bacb-0c24e56cc8f9 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T07:22:07Z |
| publishDate | 2021 |
| publisher | Wiley |
| record_format | dspace |
| spelling | oxford-uuid:2b97ea55-fc9f-49fc-bacb-0c24e56cc8f92022-10-24T08:20:37ZSynthesis, structure and reactivity of a cyapho-cyanamide saltJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:2b97ea55-fc9f-49fc-bacb-0c24e56cc8f9EnglishSymplectic ElementsWiley2021Ergöçmen, DGoicoechea, JM<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> |
| spellingShingle | Ergöçmen, D Goicoechea, JM Synthesis, structure and reactivity of a cyapho-cyanamide salt |
| title | Synthesis, structure and reactivity of a cyapho-cyanamide salt |
| title_full | Synthesis, structure and reactivity of a cyapho-cyanamide salt |
| title_fullStr | Synthesis, structure and reactivity of a cyapho-cyanamide salt |
| title_full_unstemmed | Synthesis, structure and reactivity of a cyapho-cyanamide salt |
| title_short | Synthesis, structure and reactivity of a cyapho-cyanamide salt |
| title_sort | synthesis structure and reactivity of a cyapho cyanamide salt |
| work_keys_str_mv | AT ergocmend synthesisstructureandreactivityofacyaphocyanamidesalt AT goicoecheajm synthesisstructureandreactivityofacyaphocyanamidesalt |