Download PDF
Synthesis 1992; 1992(10): 922-924
DOI: 10.1055/s-1992-26261
short paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Die "Silyl-Stobbe-Kondensation" - Synthese von Fulgimiden

Ralf Zerrer* , Gerhard Simchen
  • *Institut für Organische Chemie und Isotopenforschung der Universität Stuttgart, Pfaffenwaldring 55, D-7000 Stuttgart 80, Germany
Further Information

Publication History

Publication Date:
17 September 2002 (online)

 PDF Download  Permissions and Reprints All articles of this category

The "Silyl-Stobbe Condensation" - Synthesis of Fulgimides Organooxyalkylation of 2,5-bis(trimethylsiloxy)-1-phenylpyrrole (1) with aromatic aldehydes 2 and acetone (5) is achieved to yield 2,3-bis[aryl(trimethylsiloxy)methyl]-N-phenylsuccinimides 4 and 2-[aryl(trimethylsiloxy)methyl]-3-[1-methyl-2-(trimethylsiloxy)-ethyl]-N-phenylsuccinimides 6, respectively. By ß-elimination of trimethylsilanol the (EE)/(ZZ)-2,3-bis(arylmethylene)-N-phenylsuccinimides 7 (fulgimides) and the corresponding (E)/(Z) -2-(arylmethylene)-3-isopropylidene derivatives 8 are obtained from succinimides 4 and 6, respectively.