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It is used in the synthesis of dispiro N-Boc-protected 1,2,4-trioxane1 and (+/-)-1-(adamantan-2-yl)-2-propanamine. It is employed in reductive coupling (TiCl3/Li) which gives (adamantylidene)adamantane, an example of a general method for the synthesis of highly-substituted alkenes and in the preparation of highly-substituted alkenes by the Wittig reaction which gives poor yields with adamantanone.
Sunil Sabbani, et al. Piperidine dispiro-1,2,4-trioxane analogues.Bioorg Med Chem Lett.,2008,18(21), 5804-5808.
E Mariani, et al. (+/-)-1-(Adamantan-2-yl)-2-propanamine and other amines derived from 2-adamantanone.Farmaco Sci.,1980,35(5), 430-40.
Matthew M Meyer and Steven R Kass.Enolates in 3-D: an experimental and computational study of deprotonated 2-adamantanone.J Org Chem.,2010,75(12), 4274-4279.
Reductive coupling (TiCl3/Li) gives (adamantylidene)adamantane, an example of a general method for the synthesis of highly-substituted alkenes: Org. Synth. Coll., 7, 1 (1990).
Preparation of highly-substituted alkenes by the Wittig reaction gives poor yields with adamantanone. The route involving addition of a Grignard or alkyllithium reagent is to be preferred: J. Org. Chem., 54, 1375 (1989).