Tetrahedron letters

N-hydroxyphthalimide (NHPI)-catalyzed reaction of adamantane under nitric oxide atmosphere

S Sakaguchi, M Eikawa, Y Ishii

Index: Sakaguchi, Satoshi; Eikawa, Masahiro; Ishii, Yasutaka Tetrahedron Letters, 1997 , vol. 38, # 40 p. 7075 - 7078

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Citation Number: 31

Abstract

The reaction of adamantane under atmospheric nitric oxide in the presence of N- hydroxyphthalimide (NHPI) which serves as the radical catalyst in a mixed solvent of benzonitrile and acetic acid afforded 1-N-adamantylbenzamide as a principal product along with small amounts of 1-nitroadamantane and 1-hydroxyadamantane. On the other hand, 1- nitroadamantane was obtained in good yield upon treatment of adamantane with NO O 2.