Triethylene glycol diiodide

Compound 9 has been prepared by the latter authors using triethylene glycol diiodide and triethylene glycol diamine (see Eq. 4.11) and an alkali metal carbonate in acetonitrile solution. ... 

Diaza-crown ethers. 4,13-Diaza-18-crown ethers (1) can be prepared in one step by reaction of primary amines with triethylene glycol diiodide (equation 1). These crown... 

Newkome et al. used nucleophilic aromatic substitution to incorporate the 2,6-pyrido unit into a triazamacrocycle which was precursor to a series of cryptands (Scheme 11) <81TL3039>. The sequence uses a tertiary aminoalcohol as the nucleophile in a sodium hydride-mediated reaction with 2,6-dichloropyridine. In the second step, the tertiary amines function as nucleophiles in a reaction of triethylene glycol diiodide. The tertiary amines are converted into quaternary ammonium salts in the process. The system must be demethylated to form the neutral crown but conditions must be such that reduction of the pyridine residue does not occur. This was accomplished by using the commercial reagents L-Selectride and Super-Hydride. 

AT-benzylaza-12-crown-4 by the sodium templated reaction of benzylamine with tetraethylene glycol diiodide. Subsequent hydrogenolysis with 10% Pd/C in aqueous acetic acid gave the parent aza-12-crown-4 in a 40% yield from the diiodide. Aza-15-crown-5 can also be prepared this way however, aza-9-crown-3 cannot when triethylene glycol diiodide reacts with benzylamine, a 2 - - 2 cycliza-tion occurs to give N, yV -dibenzyldiaza-18-crown-6, as the Gokel group discovered. " ... 

ABSTRACT. Diamines and diiodides derived from diethylene glycol or triethylene glycol are condensed on alumina coated with alkali fluorides in acetonitrile to form diaza-croim ethers in good yield. Comparison of the yields suggests that the contribution of the template effect, if any, is small, and the data reflect rather increasing basicity of the solid supports in passing from LiF to KF on alumina. 

---