Electrophilic reactions at single bonds. 25. Nitration of adamantane and diamantane with nitronium tetrafluoroborate

GA Olah, P Ramaiah, CB Rao, G Sandford…

Index: Olah, George A.; Ramaiah, Pichika; Rao, Chandra B.; Sandford, Graham; Golam, Rasul; Trivedi, Nirupam J.; Olah, Judith A. Journal of the American Chemical Society, 1993 , vol. 115, # 16 p. 7246 - 7249

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Citation Number: 59

Abstract

Abstract: The slow reaction of adamantane with nitronium tetrafluoroborate at room temperature in purified, nitrilefree nitromethane or in nitroethane gives 1-nitroadamantane in 66% and 74% isolated yield, respectively. Similar reaction of diamantanegives 62% 1-and 5% 4-nitrodiamantane. Initial reaction upon aqueous workup gives 1-adamantanol with 1- fluoroadamantane, 3-fluoro-1-adamantanol, and adamantanone as byproducts. Upon ...