The Journal of Organic Chemistry

Hydrogen iodide strategy for one-pot preparation of allylic azides, nitriles, and phenyl sulfones from allylic alcohols

T Kanai, Y Kanagawa, Y Ishii

文献索引：Kanai, Takaya; Kanagawa, Yoshinori; Ishii, Yasutaka Journal of Organic Chemistry, 1990 , vol. 55, # 10 p. 3274 - 3277

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被引用次数: 42

摘要

Hydrogen iodide, HI, cleanly generated in situ from Me3SiC1/Nd and water in acetonitrile under mild conditions, was found to be an attractive reagent for the conversion of allylic alcohols into allylic iodides which serve as good allylic cation equivalent. Thus, treatment of allylic alcohols with Me3SiC1/NaI/H, 0, followed by the substitution with N;, CN-, and PhS02- ions in the same flask produced the corresponding allylic compounds bearing azide, ...