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Reactions of Neopentyl 2,2,2‐Trifluoroethanesulfonate (Tresylate) with Nucleophiles: A Model Study for the Coupling of Nucleophiles with Tresyl Agarose
Author(s) -
King James F.,
Gill Manjinder Singh
Publication year - 1995
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199516121
Subject(s) - nucleophile , agarose , chemistry , sulfur , coupling (piping) , hydrogen , carbon atom , sequence (biology) , aqueous solution , carbon fibers , computational chemistry , organic chemistry , chromatography , catalysis , materials science , biochemistry , algorithm , mathematics , ring (chemistry) , metallurgy , composite number
Not the carbon, nor the sulfur , but rather the hydrogen atom is the site of the attack of a mixture of a basic nucleophile and aqueous NaOH on neopentyl tresylate ( 1 ). The elimination–addition sequence is shown below. These observations strongly suggest that the structures assigned to affinity chromatography substrates derived from tresyl agarose should be revised.