We have developed a special alkylating agent that is very simple to synthesize and react. Stable, crystalline N-1-adamantyl-O-isopropyl-p-nitrobenzenesulfonimidate has been prepared by O-alkylation of N-1-adamantyl-p-nitrobenzenesulfonamide with  2-iodopropane and silver oxide.  This sulfonimidate rapidly converts acids to isopropyl esters, while catalysis with tetrafluoroboric acid dimethyl ether complex converts alcohols and phenols to isopropyl ethers in minutes at RT.   SNAAPTM is an acronym for Substitution, Nucleophilic of Acids, Alcohols and Phenols.   This procedure permits the synthesis of ethers with a secondary alkyl group, without the use of strong bases [Williamson reaction] and the competing E2 elimination process.

SNAAP<sup>TM</sup> isopropyl sulfonimidate alkylating agents for acids, alcohols, and phenols

243rd National Meeting (2012)

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SNAAPTM isopropyl sulfonimidate alkylating agents for acids, alcohols, and phenols

SNAAP^TM isopropyl sulfonimidate alkylating agents for acids, alcohols, and phenols