Radical Cyclization vs. Elimination in the Vitamin-B₁₂-Catalyzed Reduction of Unsaturated Bromo Acetals and Bromo Orthoesters

Authors

  • Kazumasa Yamamoto
  • Stefan Abrecht
  • Rolf Scheffold

DOI:

https://doi.org/10.2533/chimia.1991.86

Abstract

Reduction of the 2-bromoacetaldehyde acetals of cinnamyl alcohol or propargyl alcohol with Zn/NH4 in presence of catalytic amounts of B12 in DMF affords oxolanes by free radical 5-exo-cyclization and the corresponding alcohols by reductive elimination. 2-(Bromoethyl) dimethyl orthopropiolate mainly decomposes by reductive elimination and by hydrogenolysis of the bromide.

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Published

1991-03-27

How to Cite

[1]
K. Yamamoto, S. Abrecht, R. Scheffold, Chimia 1991, 45, 86, DOI: 10.2533/chimia.1991.86.

Issue

Vol. 45 No. 3 (1991): Forschung/Research

Section

Forschung

License

Copyright (c) 1991 Swiss Chemical Society

Creative Commons License

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