Reactions of living polytetrahydrofuran with amines: 2. Other tertiary amines

The reactions of living cationic polyTHF with tertiary amines have been examined. In all cases reaction results in the formation of quaternary salts which do not exchange with oxonium ions. The rates of reaction reflect the basicities of the amines; for heterocycles the order is 4-ethyl pyridine >...

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Bibliographic Details
Published in:Polymer (Guilford) 1981, Vol.22 (1), p.108-116
Main Authors: Cunliffe, A.V., Richards, D.H., Robertson, F.
Format: Article
Language:English
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Summary:The reactions of living cationic polyTHF with tertiary amines have been examined. In all cases reaction results in the formation of quaternary salts which do not exchange with oxonium ions. The rates of reaction reflect the basicities of the amines; for heterocycles the order is 4-ethyl pyridine > pyridine > isoquinoline > quinoline > acridine, and for aliphatic tertiary amines triethylamine > tributylamine > diethylaniline. Triphenylamine does not react in a timescale of several hours but the more basic amines react quantitatively under equimolar conditions at −10°C within minutes. Di-tertiary amines have been studied as linking agents and tetramethylethylenediamine (TMEDA) has been shown to be virtually quantitative. 4,4′-bipyridyl appears not to be so efficient, and pyrazine reacts only monofunctionally.
ISSN:0032-3861
1873-2291
DOI:10.1016/0032-3861(81)90084-7