Synthesis and Rearrangement Reactions of C-Alkylidene Carbohydrates

Csuk, René; Fürstner, Alois; Weidmann, Hans

doi:10.1080/07328308608062966

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Synthesis and Rearrangement Reactions of C-Alkylidene Carbohydrates

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Csuk, R., Fürstner, A., & Weidmann, H. (1986). Synthesis and Rearrangement Reactions of C-Alkylidene Carbohydrates. Journal of Carbohydrate Chemistry, 5(2), 271-285. doi:10.1080/07328308608062966.

Cite as: https://hdl.handle.net/11858/00-001M-0000-000F-F153-B

Abstract

Direct: olefinations on one hand in comparison to eliminations of aldols cf various uloses on the other each proved to be specific as to the sice of unsaturation in the branched-chain products, found to be interconvertible with one exception under a variety of conditions. Although shown to be generally equivalent to its Witcig-counterpart:, the Peterson reagent employed is liable to cause eliminations in the initial olefin. One of the branched-chain products appears to be of unusual molecular rigidity as evidenced by a large 5J coupling.