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- W2145127451 abstract "A set of unsaturated dioxanes and dioxolanes has been prepared in three steps from acetoxy-1-isoprene. When reacted with two equivalents of t-BuLi in THF, these compounds provided, under various conditions, a mixture of two types of 1,3-dienes. The first one, derived from a conjugated elimination reaction resulting in the heterocycles opening, is relatively unstable but could be trapped as an acrylate. The second one resulted probably from a [1,2]-Wittig rearrangement. The competition between these two reactions has been observed for both dioxanes and dioxolanes (but not for acyclic ketals) and is the object of a strong temperature effect, the Wittig rearrangement being favored over the elimination at room temperature. A difference between kinetic and thermodynamic deprotonation sites is proposed to be at the origin of this competition on the base of both experimental and theoretical results." @default.
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- W2145127451 date "2003-01-01" @default.
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- W2145127451 title "Conjugated elimination versus [1,2]-Wittig rearrangement of unsaturated diox(ol)anes" @default.
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- W2145127451 doi "https://doi.org/10.1016/s0040-4039(02)02568-6" @default.
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