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Synlett 1992; 1992(9): 743-744
DOI: 10.1055/s-1992-21477
DOI: 10.1055/s-1992-21477
letter
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Synthetic Use of the Organochromium(III) Intermediate in the Reductive Cyclization of Δ6,7-Unsaturated α-Bromo Esters with Chromium(II) Acetate
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Publication History
Publication Date:
08 March 2002 (online)
Δ6,7-Unsaturated α-bromo esters 1, 5 and 8 react with chromium(II) acetate to yield the cyclized organochromium(III) compounds. These species can add to benzaldehyde to give the corresponding alcohols 9 and 10, and ketone 11. In the presence of a β-alkoxy substituent, elimination to the olefins 2 and 6 occurs. The intermediate cyclic radical can be trapped with methyl acrylate, to give the adduct 7.