Tetrahedron

First synthesis of α-(3-R-1-adamantyl) sulfoacetic acids and their derivatives

A Shmailov, L Alimbarova, I Vatsouro, V Tafeenko…

Index: Shmailov, Alexander; Alimbarova, Ludmila; Vatsouro, Ivan; Tafeenko, Viktor; Shokova, Elvira; Kovalev, Vladimir Tetrahedron, 2012 , vol. 68, # 24 p. 4765 - 4772

Full Text: HTML

Citation Number: 4

Abstract

By sulfonation of 3-R-1-adamantylacetic acids 1 with H2SO4 in trifluoroacetic anhydride (TFAA), the previously unknown α-(3-R-adamantyl) sulfoacetic acids 2 were obtained. In the case of 1-adamantylacetic acid 1a, the use of∼ 1equiv of H2SO4 led to only 1- adamantylacetic acid 2a, while with an excess of the reactant the hydroxylation of the adamantane tertiary C–H bond also occurred. It is assumed that the bis (trifluoroacetyl) ...