Transposition oxy-cope assistee par le trifluoroacetate mercurique en quantite stoechiometrique et en quantite catalytique |
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Authors: | Norbert Bluthe Max Malacria Jacques Gore |
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Institution: | Laboratoire de Chimie Organique I, ERA 611 du C.N.R.S., ESCIL, Université Claude Bernard Lyon I, 43 Bd du ll Novembre 1918, 69622 Villeurbanne Cedex, France |
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Abstract: | Tertiary 1,5-hexadien-3-ols are transformed at room temperature into δ-ethylenic ketones in 35-90%, yields under two sets of conditions: treatment with one molar equivalent of mercuric trifluoroacetate followed by demercuration of the intermediate α-mercuro ketone with sodium borohydride; and treatment with 0.2 molar equivalent of t of lithium trifluoroacetate or trifluorométhansulfonate. The reactions are highly stereoselective, the E isomer of the ketone forming 80-95% of the product. The highest selectivity was observed under the second conditions. |
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