Synthesis

Chloromethanesulfonate as an Efficient Leaving Group: Rearrangement of the Carbon-Carbon Bond and Conversion of Alcohols into Azides and Nitriles

T Shimizu, T Ohzeki, K Hiramoto, N Hori, T Nakata

文献索引：Shimizu, Takeshi; Ohzeki, Tomoya; Hiramoto, Katsuya; Hori, Nobuyuki; Nakata, Tadashi Synthesis, 1999 , # 8 p. 1373 - 1385

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被引用次数: 17

摘要

Abstract: The chloromethanesulfonate (monochlate) served as an efficient leaving group for rearrangement of the carbon–carbon bond and conversion of alcohols into azides and nitriles. The treatment of the monochlate 16a with zinc acetate in dioxane at 90 C effected migration of the 4a-methyl group to give alkene 17a. Upon similar treatment of the monochlates 22a, 25a, 28a, and 31a with zinc acetate, the carbon–carbon bonds ...