Aromatic substitution. 58. Boron tris (triflate)-catalyzed adamantylation of benzene and toluene with 1-and 2-haloadamantanes and adamantanoyl chlorides. …

GA Olah, O Farooq, SMF Farnia…

Index: Olah, George A.; Farooq, Omar; Farnia, S. Morteza F.; Wu, An-hsiang Journal of Organic Chemistry, 1990 , vol. 55, # 5 p. 1516 - 1522

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Citation Number: 15

Abstract

Interconversion of isomeric 2-phenyl (tolyl) adamantanes into the corresponding 1-phenyl (toly1) adamantanes was observed through intermolecular isomerization involving adamantyl cations and adamantane, which is formed in significant amount in all the reactions. Decarbonylative alkylation of aromatics with adamantanoyl chlorides was also investigated. Adamantanoylated aromatics were formed only in very low amounts, the ...