Chirality Transfer in the Formation of Poly(oxymethylene) Helices by Anionic Polymerization

Abstract

In this article, we present the synthesis of a series of oligo(oxymethylenes) capped with 1‐phenylethanol and MeOH. The anionic condition affords enantiomerically pure oligo(oxymethylene) oligomers, while the cationic oligomerization leads to a racemic mixture of the oligo(oxymethylene) chain.

Formaldehyde—A Key Monad of the Biomolecular System

“…In one experiment significant asymmetric 1,10-induction of chirality was obtained in a Grignard reaction along the oxymethylene chain [ 80 ]. Experiments also showed that our diastereoselectivity rule also applied across an oligomeric polyoxymethylene chain [ 79 , 81 ]. In fact the helical conformation of the -O-C-O- sequence in polyformaldehyde resembles rather the atomic arrangement of -O-Si-O- helices in a quartz crystal or atomic arrangements in other inorganic crystals [ 79 ].…”