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Synthesis and polymerization behavior of 2,3-dihydro-1,4-dioxin-2-one and its 3-methyl derivative

✍ Scribed by Günter Wulff; Kai Jakoby

Publisher: John Wiley and Sons
Year: 1996
Tongue: English
Weight: 377 KB
Volume: 197
Category: Article
ISSN: 1022-1352
DOI: 10.1002/macp.1996.021970714

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✦ Synopsis

Abstract

The hitherto unknown 2,3‐dihydro‐1,4‐dioxin‐2‐one (7) and its 3‐methyl derivative 8 have been synthesized for the first time. The olefinic double bond is inserted into the saturated 1,4‐dioxanone precursors 3 and 6a/b by a retro‐Diels‐Alder reaction in the last step of the synthesis. The 1,4‐dioxanone systems of 3 and 6 are prepared by reacting a vicinal dialkoxide with α‐halogenated acyl halides, thus forming the ester and the ether bond in a one‐pot reaction. Monomers 7 and 8 are polymerized by cationic initiation. The resulting products undergo fragmentation to form oligomers in the presence of protic solvents, indicting that ring‐opening polymerization of the δ‐lactone apparently leads to polyester chain segments.

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