Abnormal PdII-Catalyzed Cyclization of 1-Methyl-1-(2-trimethylsilylethynyl)-2-propenyl Acetate

Authors

  • Valentin Rautenstrauch Research Laboratories, Firmenich SA Case Postale 239, CH-1211 Genève 8
  • Ulrich Burger Département de Chimie Organique, Université de Genève
  • Philippe Wirthner Département de Chimie Organique, Université de Genève

DOI:

https://doi.org/10.2533/chimia.1985.225

Abstract

PdCl2(MeCN)2-catalyzed cyclization of 1-methyl-1-(2-trimethylsilylethynyl)-2-propenyl acetate (4) afforded 5-methyl-2-trimethylsilyl-1,4-cyclopentadienyl acetate (5) and 3-methyl-2-trimethylsilyl-1,3-cyclopentadienyl acetate (6) in a 1.2:1 ratio and ≥80% combined yield. The formation of 5 was anticipated by analogy with previous work but that of 6 is unprecedented. Compounds 5 and 6 were trapped with N-phenylmaleimide and their fate in the absence of the trapping agent elucidated.

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Published

1985-08-31

Issue

Vol. 39 No. 7-8 (1985): Forschung/Research

Section

Articles

License

Copyright (c) 1985 Valentin Rautenstrauch

Creative Commons License

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

How to Cite

[1]
V. Rautenstrauch, U. Burger, P. Wirthner, Chimia 1985, 39, 225, DOI: 10.2533/chimia.1985.225.