Lepore Salvatore D, Bhunia Anjan K, Cohn Pamela
Department of Chemistry, Florida Atlantic University, Boca Raton, Florida 33431-0991, USA.
J Org Chem. 2005 Sep 30;70(20):8117-21. doi: 10.1021/jo051241y.
[Chemical reaction: See text] The synthesis and unique reactivity of a series of arylsulfonate-based nucleophile assisting leaving groups (NALG) containing oligomeric ether units (including crown ethers) attached to the arylsulfonyl ring in the ortho orientation are described. The reactions of a variety of these ether-containing alkyl sulfonates with metal halides proceeded at substantially greater rates than electronically similar sulfonates. These ether-containing leaving groups also displayed marked selectivity for lithium halides relative to the corresponding sodium and potassium salts in nucleophilic displacement reactions.
[化学反应：见正文] 描述了一系列基于芳基磺酸盐的亲核试剂辅助离去基团（NALG）的合成及其独特反应性，这些离去基团包含以邻位连接到芳基磺酰环上的低聚醚单元（包括冠醚）。多种这些含醚烷基磺酸盐与金属卤化物的反应速率比电子性质相似的磺酸盐快得多。在亲核取代反应中，相对于相应的钠盐和钾盐，这些含醚离去基团对卤化锂也表现出显著的选择性。
