Journal of the American Chemical Society p. 864 - 867 (1988)
Update date:2022-08-11
Topics:
Farooq, Omar
Marcelli, Mike
Prakash, G. K. Surya
Olah, George A.
The superacid-catalyzed reaction of adamantane with carbon monoxide was investigated. 1-Adamantanecarboxaldehyde together with 1-adamantaneecarboxylic acid and 1-adamantanol (the products of the reaction of intermediate 1-adamantyl cation) was obtained.The mechanism of the formation of 1-adamantanecarboxaldehyde by electrophilic formylation involving ?-insertion of the formyl cation is indicated.This is contrasted by the competing protolytic ionization of adamantane to 1-adamantyl cation which gives with CO 1-adamantanoyl cation and subsequently 1-adamantanecarboxylic acid (Koch-Haaf reaction) or by hydrolysis 1-adamantanol.
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