Über Benzyl‐tetramethyl‐ammonium

200 Years of Lithium and 100 Years of Organolithium Chemistry

“…In 1913 he took a position at the University of Jena and focused first on addition compounds of sodium and olefins as well as polycyclic aromatic hydrocarbons (“ Schlenk addition compounds”). In 1917 he published the first synthesis of organolithium compounds (MeLi, EtLi, PhLi) from highly toxic organomercury compounds and Li metal (Scheme ) …”

“…Lithium rapidly developed a rich organometallic chemistry. It started with the first synthesis of organometallic lithium compounds by Wilhelm Schlenk in 1917 . Besides several congeneric sodium compounds he presented the successful isolation of methyllithium (LiCH 3 ), ethyllithium (LiC 2 H 5 ), and phenyllithium (LiC 6 H 5 ).…”

Trans‐Metal‐Trapping: Concealed Crossover Complexes En Route to Transmetallation?

“…His protégé Wanklyn (1834–1906) then pioneered ate compounds by pairing diethylzinc with potassium . Not long afterwards, Schlenk (1879–1943) employed the same methodology to prepare the first organolithium compounds (Scheme ), which today, together with Grignard reagents, are popular commercial starting materials that readily undergo transmetallation with halogeno or pseudohalogeno complexes of transition metals, Group 13 and 14 elements. Along with its significance as a preparative method, organic ligand transfer between two metal complexes is present in numerous metal‐mediated organic transformations including polymerization of alkenes, carbometallation and cross‐coupling reactions…”

Schlenk in Tübingen

“…Die Synthese der ersten Organolithiumverbindungen, darunter mikrokristallines Methyllithium und einkristallines Ethyllithium, über Transmetallierungsreaktionen mit den entsprechenden Quecksilberalkylen, und die Charakterisierung der Natriumalkyle sind Meilensteine der Organometallchemie 15. Beeindruckend ist auch die Isolierung von hochexplosivem Mononatriumhydrazid und dessen Entschärfung über eine Alkoholyse‐Reaktion 16…”