Behaviour of Arylazo tert-Butyl Sulfides with Ketone Enolates. Competition between SRN1 α-arylation and Azocoupling Reactions.
作者:Carlo Dell'Erba、Marino Novi、Giovanni Petrillo、Cinzia Tavani
DOI:10.1016/s0040-4020(01)88144-8
日期:——
room temperature, with potassium acetone enolate to give good yields of 1-aryl-2-propanones via spontaneous SRN1 dark reactions, α-Phenylation of pinacolone and acetophenone enolates by 1a likewise occurs in excellent yields. In agreement with the involvement of an electron-transfer catalyzed chain process, the reaction of the 4-bromo derivative 1n with pinacolone enolate gives mainly the bis-substitution
(Z)-芳基偶氮叔丁基硫化物1a-i在DMSO中和室温下与丙酮烯醇钾反应,通过自发的S RN 1暗反应,频哪酮的α-苯甲酰化反应生成1-芳基-2-丙烷的良好收率苯乙酮烯醇化1a的收率也很高。与电子转移催化链过程的参与相一致,4-溴衍生物1n与频哪酮烯醇酸酯的反应主要产生双取代产物13。在偶氮硫化物1j–m中,芳基化途径与碱基诱导的硫醇消除竞争,最终取决于偶氮硫化物的结构而导致吲唑8或11和/或2-氧代丙醛芳基腙9,10或12。