Über den Anwendungsbereich gezielter Catenansynthesen. Verbesserte Synthese von zweifach überbrückten 1,4‐Diaminobenzol‐Derivaten

Abstract

Scope and Limitations of Directed Syntheses of Catenanes. Improved Synthesis of Double-Bridged 1,4-Diaminobenzene DerivativesIn a one-flask reaction the double-bridged 1,4-diaminobenzene derivative 4a is synthesized in different solvents from 1,4-diaminobenzene and 1 ,lo-dibromodecane. The highest yields are obtained in 2-pentanol and tert-amyl alcohol. -In a multi-step reaction sequence the [2]-precatenane 10 is synthesised starting from 3,5-tetracosamethylenepyrocatechol (7) and 1,19-dichloro-10-nonadecanone (8). The attempted transformation of this compounds into the corresponding [2]-catenane by splitting the bonds between the aromatic nucleus and the bridgehead atoms was unsuccessful.

Synthesis and rotational dynamics of diazamacrocycles having bridged 1,4-naphthylene as framed molecular rotors

“…[6][7][8][9] The first diazamacrocycle with a bridged phenylene C10 was reported as a molecular vase by Luttringhaus 6 in 1947. Schill 7,8 reported C10 and C12 as model precursors for catenanes, while synthetic protocols such as the direct cyclization of p-phenylenediamine with α,ω-dihaloalkanes in the presence of K 2 CO 3 were established in 1983. Our group recently reported the synthesis, crystal structure, and redox properties of C10, C12, and C14.…”