Arylsulfonate-based nucleophile assisting leaving groups.
[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.
Lepore
Salvatore D
SD
Department of Chemistry, Florida Atlantic University, Boca Raton, Florida 33431-0991, USA. slepore@fau.edu
Bhunia
Anjan K
AK
Cohn
Pamela
P
D001190:Arylsulfonates / Q000737:chemistry*; D001565:Benzoates / Q000138:chemical synthesis / Q000737:chemistry; D018360:Crystallography, X-Ray; D004987:Ethers; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D011092:Polyethylene Glycols / Q000737:chemistry
D001190:Arylsulfonates; D001565:Benzoates; D004987:Ethers; D007202:Indicators and Reagents; D011092:Polyethylene Glycols