Zur Synthese von Aminocycliten

Abstract

Aus Rhodizonsäure-1.4-diimid wurde durch katalytische Hydrierung in schwefelsaurer Lösung das Sulfat eines 1.4-Diamino-2.3.5.6-tetrahydroxy-cyclohexans erhalten. In gleicher Weise ließ sich Triamino-phloroglucin in ein 1.3.5-Triamino-2.4.6- trihydroxy-cyclohexan überführen

1,3,5‐Triamino‐1,3,5‐trideoxy‐cis‐inositol, a New Ligand with a Remarkable Versatility for Metal Ions. Part 2. Safe and efficient ligand preparation and structure of the free ligand and the CoIII complex

“…-1,3,5-Triamino-l,3,5-trideoxy-cis -inositol (taci) received attention lately owing to the unusual acidity of the OH groups and the metal-binding properties [l-31. taci has first been prepared by Quadbeck and Rohm in 1956 [4], and the (all-&)-configuration has been elucidated 1966 by Lichtenthaler and Leinert [5]. Despite of the remarkable molecular structure -cyclohexane derivatives with three substituents in a stable syn -1,3,5-triaxial arrangement are rare -no further investigations on this compound have been reported until 1990.…”

Reversible Energy Storage in Layered Copper-Based Coordination Polymers: Unveiling the Influence of the Ligand’s Functional Group on Their Electrochemical Properties

“…For the preparation of the TAPG ligand, the synthesis was carried by acidic nitration of phloroglucinol followed by reduction with hydrogen catalyzed by Pd supported on carbon (1% wt) (Scheme S1) following the report from Quadbeck and Roḧm. 32 The successful synthesis of the targeted TAPG ligand was confirmed by 1 H NMR and 13 C NMR (Figures S1 and S2). It has to be noted that for the synthesis of the TAPG ligand, potentially explosive trinitrobenzene derivates are produced, and in consequence, maximized safety measures, as well as synthesis of minimum as possible quantities of the materials synthesized, are encouraged.…”

“…Finally, the material was dried overnight under vacuum at 110 °C. For the preparation of the TAPG ligand, the synthesis was carried by acidic nitration of phloroglucinol followed by reduction with hydrogen catalyzed by Pd supported on carbon (1% wt) (Scheme S1) following the report from Quadbeck and Röhm . The successful synthesis of the targeted TAPG ligand was confirmed by 1 H NMR and 13 C NMR (Figures S1 and S2).…”

The Interplay of Hydrogen Bonding and Multiple Metal Binding – A New Cyclic Polyaminopolyalcohol Ligand as Building Block for the Construction of Microporous, Supramolecular Networks

“…The tachol, daci5a and ddci5b ligands were prepared by hydrogenation of P2 , P3 11a and P4 11b (5 bar H 2 , 20–45 °C, aqueous H 2 SO 4 ) using a Pt/Rh‐on‐C catalyst (see Supporting Information). Caution!…”

“…Cyclohexane‐based PAPA ligands have not received wide attention, although they can be readily obtained bystereospecific hydrogenation of aromatic precursors (Scheme ) 5. Metal binding of 1,3,5‐triamino‐1,3,5‐trideoxy‐ cis ‐inositol (taci) with its four distinct binding sites (i)–(iv) has already been studied;4 however, the coordination chemistry of further examples such as all‐ cis ‐2,4,6‐triaminocyclohexanol (tachol), 1,3‐diamino‐1,2,3‐trideoxy‐ cis ‐inositol (daci), and 1,4‐diamino‐1,4‐dideoxy‐ cis ‐inositol (ddci) has not yet been reported; ddci has been prepared many years ago,5b and we confirmed now its all‐ cis configuration by a crystal structure analysis;6 tachol, the hydrogenation product of picric acid, appeared to be completely unknown up to date. Representing a substructure of the taci geometry, metal binding of tachol is restricted to a type (i) or type (ii) mode.…”