Stereochemistry of 2, 6??Diaminoadamantane Salts: Transannular Interactions

…, O Trapp, K Mlinarić??Majerski

Index: Glaser, Robert; Steinberg, Avital; Sekutor, Marina; Rominger, Frank; Trapp, Oliver; Mlinaric-Majerski, Kata European Journal of Organic Chemistry, 2011 , # 19 p. 3500 - 3506

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Citation Number: 4

Abstract

Abstract A series of bisprimary, bistertiary, and bisquaternary adamantane-2, 6-diammonium salts were synthesized from adamantane-2, 6-dione starting material. Conversion of the dione to a dioxime followed by H 2/PtO 2 hydrogenation afforded 2, 6-diaminoadamantane dihydrochloride 2a. Reductiveamination of 2a with aqueous formaldehyde (H 2/PtO 2) gave rac-N, N, N′, N′-tetramethyl-2, 6-diaminoadamantane dihydrochloride salt 3. Diffusion ...