Neuartige Addukte aus Maleinimiden und Schiff-Basen durch «dipolare Spiro-Bisaddition»

Authors

  • L. Zirngibl Forschungsabteilung der Siegfried AG, CH-4800 Zofingen
  • Th. Wagner-Jauregg Forschungsabteilung der Siegfried AG, CH-4800 Zofingen
  • C.W. Paris Forschungsabteilung der Siegfried AG, CH-4800 Zofingen
  • Q. Ahmed Forschungsabteilung der Siegfried AG, CH-4800 Zofingen
  • E. Pretsch Institut für organische Chemie der ETH Zürich

DOI:

https://doi.org/10.2533/chimia.1971.227

Abstract

Schiff bases prepared from an aromatic or heterocyclic aldehyde and an amine add 2 molecules of maleimides in a novel dipolar addition giving 1 : 2-adducts which comprise newly formed tricyclic five-membered spiro structures III. Their stereochemistry (IIIA, IIIA' and IIIB) is discussed based on NMR-data. An azomethine ylid transition state (V) has been proposed and verified by reaction with a second dipolarphile yielding again a novel spiro ring. This new type of a 1,3-dipolar addition also plays a role in the formation of a 1:3-adduct from 4-vinylpyridine and N-butyl-maleimide.

Downloads

Published

1971-07-31

Issue

Vol. 25 No. 7 (1971): Forschung/Research

Section

Kurze Mitteilungen

License

Copyright (c) 1971 L. Zirngibl

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

How to Cite

[1]
L. Zirngibl, T. Wagner-Jauregg, C. Paris, Q. Ahmed, E. Pretsch, Chimia 1971, 25, 227, DOI: 10.2533/chimia.1971.227.