Arylsulfonate-based nucleophile assisting leaving groups |
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Authors: | Lepore Salvatore D Bhunia Anjan K Cohn Pamela |
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Institution: | Department of Chemistry, Florida Atlantic University, Boca Raton, Florida 33431-0991, USA. slepore@fau.edu |
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Abstract: | 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. |
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