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Arylsulfonate-based nucleophile assisting leaving groups.

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.

SUBMITTER: Lepore SD

PROVIDER: S-EPMC3563673 | biostudies-literature | 2005 Sep

REPOSITORIES: biostudies-literature

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Arylsulfonate-based nucleophile assisting leaving groups.

Lepore Salvatore D SD Bhunia Anjan K AK Cohn Pamela P

The Journal of organic chemistry 20050901 20

[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 ...[more]

PMID: 16277337

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