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Tris(3,6-dioxaheptyl)amine acts as a phase transfer catalyst used in the preparation of 1,3-dideaza-2'-deoxyadenosine and related benzimidazole 2'-deoxyribonucleosides. It is also used as an intermediate in the synthesis of telithromycin. Further, it is used in the oxidation of arylmethanols under phase-transfer conditions. In addition to this, it acts as a cryptand during phase-transfer glycosylation of 2-amino-4-methoxy-7H-pyrrolo[2,3-d]pyrimidine.
Acyclic solid-liquid phase-transfer catalyst (see Appendix 2).
Solubilizes salts of alkali metals and of transition metals, e.g. PdCl2, RuCl3 and RhCl3, allowing these to be used in hydrogenation reactions: Synth. Commun., 19, 2833 (1989).
Forms isolable 2:1 complexes with Grignard reagents: Tetrahedron, 45, 171 (1989).
Accelerates dehydrobromination of alkyl halides in the presence of KOH: Org. Synth. Coll., 9, 539 (1998). For use in the Wittig reaction, see Cyclopropyltriphenylphosphonium bromide, B25102.
Has been used in a number of aromatic nucleophilic substitution reactions:
In studies of solvent-free SNAr reactions, TDA-1 was found to be the best catalyst: Synth. Commun., 20, 2855 (1990); Heterocycles, 32, 1947 (1991). In combination with CuCl, is also a useful catalyst in the Ullmann aryl ether synthesis: J. Org. Chem., 50, 3717 (1985). An improved N-arylation of amides utilizes a catalyst combination of CuCl and TDA-1 (5:1): Synthesis, 312 (1989).
For use in a stereospecific glycosylation reaction of a pyrimidine base, see: Helv. Chim. Acta, 71, 1573 (1988).
Quick, M. P.; Wünsch, B. Synthesis of hydrogenated 2-benzazepin-1-ones by the addition of aryllithium intermediates to isocyanates. Tetrahedron: Asymmetry 2015, 26 (5-6), 276-280.
Li, H.; Pang, Z.; Gao, P.; Wang, L. Fe(III)-catalyzed grafting copolymerization of lignin with styrene and methyl methacrylate through AGET ATRP using triphenyl phosphine as a ligand. RSC Adv. 2015, 5 (67), 54387-54394.
Hazard Statements: H315-H319
Causes skin irritation. Causes serious eye irritation.
Precautionary Statements: P280a-P264-P305+P351+P338-P321-P332+P313-P337+P313
Wear protective gloves and eye/face protection. Wash thoroughly after handling. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Specific treatment (see label). If skin irritation occurs: Get medical advice/attention. If eye irritation persists: