Nucleophilic esterolytic and displacement reactions of a micellar thiocholine surfactant

RA Moss, GO Bizzigotti, CW Huang

Index: Moss, Robert A.; Bizzigotti, George O.; Huang, Ching-Wen Journal of the American Chemical Society, 1980 , vol. 102, # 2 p. 754 - 762

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Citation Number: 19

Abstract

Results Synthesis. Choline surfactant 5 (16-OH) was converted to its triflate derivative with triflic anhydride in CHzCIz/pyridine. Self-phase-transfer catalytic conversion" of the triflate to 6 (1 6-SAc, X= OTf) was achieved'by stirring the CH2C12 SO-lution with excess aqueous sodium thioacetate. Ion exchange of 6 to its water-soluble chloride form, followed by deprotection with deoxygenated 3 N aqueous HCI, lyophilization, and recrystallization ...