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PubMed · 16277337

Arylsulfonate-based nucleophile assisting leaving groups.

Salvatore D Lepore·Anjan K Bhunia·Pamela Cohn
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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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ArylsulfonatesBenzoatesCrystallography, X-RayEthersIndicators and ReagentsMagnetic Resonance SpectroscopyModels, MolecularMolecular StructurePolyethylene GlycolsJournal ArticleResearch Support, N.I.H., ExtramuralResearch Support, Non-U.S. Gov't

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Salvatore D Lepore, Anjan K Bhunia, Pamela Cohn. 2005-09-30. Arylsulfonate-based nucleophile assisting leaving groups.. https://doi.org/10.1021/jo051241y

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