The Journal of Organic Chemistry

Synthesis of adamantane derivatives. 54. Synthesis of novel 4-azahomoadamantano [3, 4]-fused heterocycles via hydrocyanation of 4-azahomoadamant-3-ene

T Sasaki, S Eguchi, T Okano

Index: Sasaki, Tadashi; Eguchi, Shoji; Okano, Takashi Journal of Organic Chemistry, 1981 , vol. 46, # 22 p. 4474 - 4477

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Citation Number: 6

Abstract

Photolysis of 1-azidoadamantane (1) in an aqueous NaCN-n-hexane two-phase system with Adogen 464 as a phase-transfer catalyst gave 3-cyano-4-azahomoadaantane (3), a hydrocyanation product of 4-azahomoadamant-3-ene (2). A1C13-catalyzed decomposition of 1 in the presence of trimethylsilyl cyanide also afforded 3. 3 gave the corresponding amino acid 6 and ita ester 7. 4-Azahomoadamantano [3, 4]-fused hydantoin, ...