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Polyamides and polyesters containing 2,4:3,5-di-O-methylene-L-idaroyl residues

✍ Scribed by A. H. A. Tinnemans; H. A. Budding; F. Stein; J. C. Venekamp

Book ID: 104589160
Publisher: Elsevier Science
Year: 2010
Tongue: English
Weight: 601 KB
Volume: 109
Category: Article
ISSN: 0165-0513
DOI: 10.1002/recl.19901090309

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✦ Synopsis

Abstract

Electrochemical oxidation of 2,4:3,5‐di‐O‐methylene‐D‐gluconic acid in strong alkaline medium afforded a mixture of 2,4:3,5‐di‐O‐methylene‐D‐glucaric acid 4 and 2,4:3,5‐di‐O‐methylene‐L‐idaric acid 1 in a 1/8 ratio with a current efficiency of 53%. Force‐field calculations using Allinger's molecular mechanics program MM2p85 on 1 and 4 indicate that these cis‐fused tetrahydro‐[1,3]dioxino[5,4‐d]‐1,3‐dioxin ring systems possess an O‐inside conformation with a steric energy of 110.3 and 123.5 kJ·mol^−1^, respectively. Their conformation was confirmed by 400‐MHz ^1^H‐ and 100‐MHz ^13^C NMR measurements.

A series of polycondensates were prepared by homogeneous solution polymerisation of 1 with an aromatic diol or aromatic diamine, which were analyzed by DSC and TGA.

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