Radical Cyclization vs. Elimination in the Vitamin-B₁₂-Catalyzed Reduction of Unsaturated Bromo Acetals and Bromo Orthoesters
DOI:
https://doi.org/10.2533/chimia.1991.86Abstract
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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1991-03-27
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Copyright (c) 1991 Swiss Chemical Society
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How to Cite
[1]
K. Yamamoto, S. Abrecht, R. Scheffold, Chimia 1991, 45, 86, DOI: 10.2533/chimia.1991.86.