Preparation and Reactions of Quaternary Ammonium Salts Derived from cis-2, 5-Bis-(hydroxymethyl)-tetrahydrofuran Ditosylate

AC Cope, EE Schweizer

Index: Cope; Schweizer Journal of the American Chemical Society, 1959 , vol. 81, p. 4577,4581

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Citation Number: 5

Abstract

The isolation of 3-methyl-8-oxa-3-azabicyclo [3.2. l] octane methobromide (VI, R= CH3)(50%) from the product ob-tained from dimethylamine and cis-2, 5-bis-(hydroxymethyl)- tetrahydrofuran ditosylate (I) demonstrates the existence of the corresponding quaternary tosylate (11, R= CHa) in the initial reaction mixture. The reaction also yields a significant amount of trimethylamine, formed by alkylation of dimethylamine by the quaternary ...