Nonselective Bromination−Selective Debromination Strategy:  Selective Bromination of Unsymmetrical Ketones on Singly Activated Carbon against Doubly Activated Carbon

We have found a new synthetic method for the preparation of the α-bromoketones that are brominated in the less activated terminal position of unsymmetrical ketones. Brominations in short reaction times (kinetically controlled) provided internally brominated compounds as a major product. However, bro...

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Veröffentlicht in:Organic letters 2003-02, Vol.5 (4), p.411-414
Hauptverfasser: Choi, Han Young, Chi, Dae Yoon
Format: Artikel
Sprache:eng
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Zusammenfassung:We have found a new synthetic method for the preparation of the α-bromoketones that are brominated in the less activated terminal position of unsymmetrical ketones. Brominations in short reaction times (kinetically controlled) provided internally brominated compounds as a major product. However, brominations in longer reaction times (thermodynamically controlled) gave more of the terminally brominated compound through the reversible reaction by Br2 and produced hydrogen bromide. Several brominated compounds at the terminal position were successfully prepared through the new synthetic route.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0271638