HYDROGEN IODIDE STRATEGY FOR ONE-POT PREPARATION OF ALLYLIC AZIDES, NITRILES, AND PHENYL SULFONES FROM ALLYLIC ALCOHOLS

被引：49

作者：

KANAI, T ^{[1
]}

KANAGAWA, Y ^{[1
]}

ISHII, Y ^{[1
]}

机构：

[1] KANSAI UNIV,DEPT APPL CHEM,SUITA,OSAKA 564,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 10期

关键词：

D O I：

10.1021/jo00297a053

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Hydrogen iodide, HI, cleanly generated in situ from Me3SiCl/NaI 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 Me3SiCl/NaI/H2O, followed by the substitution with N3-, CN-, and PhS02-ions in the same flask produced the corresponding allylic compounds bearing azide, cyano, and phenyl sulfonyl functionalities in fair yields. This method provides a useful procedure for the preparation of allylic compounds from easily available allylic alcohols. © 1990, American Chemical Society. All rights reserved.

引用

页码：3274 / 3277

页数：4

共 19 条

[1]

BLATT AH, 1956, ORG SYNTH, V1, P46

[2]

CAREY FA, 1985, ADV ORGANIC CHEM A, P265

[3]

COLVIN EW, 1981, SILICON ORGANIC SYNT, P288

[4] THERMAL REARRANGEMENT OF ALLYL-TYPE SULFOXIDES, SULFONES AND SULFINATES [J].