Nachweis der Löslichkeit des Acetylidions C₂²⁻ – Synthese und Kristallstrukturen von K₂C₂⋅2 NH₃, Rb₂C₂⋅2 NH₃ und Cs₂C₂⋅7 NH₃

Abstract

Kohlenstoffanionen in Lösung: C22−‐Hanteln sind in Festkörperverbindungen seit langem bekannt. Mit der Kristallisation der Titelverbindungen konnte nun gezeigt werden, dass Acetylidionen auch in Lösung existieren. Dadurch rückt eine Chemie mit kleinen gelösten Kohlenstoffanionen in greifbare Nähe.

Crystal structure of rubidium peroxide ammonia disolvate

“…3). This structural motif can also be observed in potassium acetylide K 2 C 2 (Hamberger et al, 2012). The peroxide bond length was determined to be 1.530 (11) Å .…”

Acetylide Ion (C22−) as a Synthon To Link Electrophiles and Nucleophiles: A Simple Method for Enaminone Synthesis

“…[2][3][4] Given the demand for the alkyne functionality and its nucleophilic properties, the acetylide ion could play an important role in modern organic synthesis. [5] It was reported previously that the acetylide dianion can act as a mild nucleophile to link two identical electrophiles, such as aryl halides (Sonogashira coupling) [2] or two carbon dioxide molecules, [6] or an aldehyde with an amine (Scheme 1).…”

Acetylide Ion (C22−) as a Synthon To Link Electrophiles and Nucleophiles: A Simple Method for Enaminone Synthesis

“…, has been known for many years, [1] the direct use of metal acetylides (M I 2 C 2 or M II C 2 ) in organic synthesis is quite rare, mainly because of the low solubility of metal acetylides in common organic solvents. [2][3][4] Given the demand for the alkyne functionality and its nucleophilic properties, the acetylide ion could play an important role in modern organic synthesis. [5] It was reported previously that the acetylide dianion can act as a mild nucleophile to link two identical electrophiles, such as aryl halides (Sonogashira coupling) [2] or two carbon dioxide molecules, [6] or an aldehyde with an amine (Scheme 1).…”