Issue 95, 2015

New insights into synthesis and oligomerization of ε-lactams derived from the terpenoid ketone (−)-menthone

Abstract

Two regioisomeric lactams, which are derived from terpenoid ketone (−)-menthone in two steps, are oligomerized in an easy acid-induced procedure to obtain oligoamides that contain alkyl groups and stereocenters; for this, a nucleophilic oligomerization via a non-ionic propagating site (neutral conditions) and a polycondensation are also possible. Furthermore, a regioselective synthesis is demonstrated where (−)-menthone is transformed into one of these lactams in a one-step procedure via Beckmann rearrangement without isolation of any oxime intermediate using the reagent hydroxylamine-O-sulfonic acid (HOSA). These concise oligoamide syntheses smooth the way to novel sustainable long-chain polyamides with highly interesting structures.

Graphical abstract: New insights into synthesis and oligomerization of ε-lactams derived from the terpenoid ketone (−)-menthone

Supplementary files

Article information

Article type
Paper
Submitted
05 Aug 2015
Accepted
04 Sep 2015
First published
04 Sep 2015

RSC Adv., 2015,5, 77699-77705

Author version available

New insights into synthesis and oligomerization of ε-lactams derived from the terpenoid ketone (−)-menthone

M. Winnacker, A. Tischner, M. Neumeier and B. Rieger, RSC Adv., 2015, 5, 77699 DOI: 10.1039/C5RA15656D

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