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Crich D, Barba GR. Efficient one-pot conversion of carbonyl compounds to their alpha,beta-unsaturated derivatives using a recoverable, minimally fluorous organoselenium reagent. Org Lett. 2000;2(7):989-91doi: 10.1021/ol005669p.
Crich, D., & Barba, G. R. (2000). Efficient one-pot conversion of carbonyl compounds to their alpha,beta-unsaturated derivatives using a recoverable, minimally fluorous organoselenium reagent. Organic letters, 2(7), 989-91. https://doi.org/10.1021/ol005669p
Crich, and Barba. "Efficient one-pot conversion of carbonyl compounds to their alpha,beta-unsaturated derivatives using a recoverable, minimally fluorous organoselenium reagent." Organic letters vol. 2,7 (2000): 989-91. doi: https://doi.org/10.1021/ol005669p
Crich D, Barba GR. Efficient one-pot conversion of carbonyl compounds to their alpha,beta-unsaturated derivatives using a recoverable, minimally fluorous organoselenium reagent. Org Lett. 2000 Apr 06;2(7):989-91. doi: 10.1021/ol005669p. PMID: 10768204.
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Org Lett. 2000 Apr 06;2(7):989-91. doi: 10.1021/ol005669p.

Efficient one-pot conversion of carbonyl compounds to their alpha,beta-unsaturated derivatives using a recoverable, minimally fluorous organoselenium reagent.

Organic letters

Crich, Barba

Affiliations

  1. Department of Chemistry, University of Illinois at Chicago 60607-7061, USA. [email protected]

PMID: 10768204 DOI: 10.1021/ol005669p

Abstract

A protocol for the preparation of a fluorous arylselenenyl chloride is described. This selenenyl chloride may be used for the direct alpha-selenation of ketones and, following oxidation and syn-elimination, formation of alpha,beta-unsaturated carbonyl compounds. Treatment of the crude reaction mixtures with sodium metabisulfite reduces the various selenium species to the diaryl diselenide, which is then recovered in high yield by continuous fluorous extraction.

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