Download PDF
Synthesis 1989; 1989(5): 367-372
DOI: 10.1055/s-1989-27254
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.

Synthese und Eigenschaften von 3-Acylmethylen -2-(2-hydroxy-1-alkenyl)-1-phenylcyclopropen, einer neuartigen Klasse von stabilisierten Triafulvenen

Theophil Eicher* , Volker Huch, Volker Schneider, Michael Veith
  • *Fachbereich 13, Anorganische und Organische Chemie, Universität des Saarlandes, D-6600 Saarbrücken 11, Federal Republic of Germany
Further Information

Publication History

Publication Date:
17 September 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

Synthesis and Properties of 3-Acylmethylene-2-(2-hydroxy-1-alkenyl)-1-phenylcyclopropenes, a New Class of Stabilized Triafulvenes Triavulvenes of type 9 are obtained by reaction of dichloro(phenyl)-cyclopropenylium cation 7 with two equivalents of silyl enol ethers 8. They are characterized by means of their spectroscopic data and by X-ray analysis of 9c as cyclic 7-hydroxy-2,4,6-heptatrien-1-one systems with intramolecular H-bonding (type 10) representing a new type of stabilized methylenecyclopropenes. Similar compounds are formed by reaction of 7 with 4-methoxytoluene and 2-methoxynaphthalene (12, 15) or with dimedone (13). The cyclopropenone 16 is obtained as main product of the 1:1 reaction of 7 and 8a, it isomerizes thermally to give the α-pyrone 17.