2-(l-Adamantyl)-2-hydroximinoacetonitrile Oxide (IV). A solution of K3Fe(CN) 6 (7.4 g, 22.5 mmole) and KOH (1.26 g, 22.5 mmole) in water (67 ml) was added dropwise with stirring to a solution of glyoxime la (2 g, 9 mmole) in ether (60 ml). The reactionmixture was stirred for 2 h at 25~ the ether layer separated, wahsed with water, and dried. After removal of ether the residue was washed with pentane to give IV (1.4 g) which was chromatographed using CCl~-acetone (6:1) [7].
4-(l-Adamantyl)-3-aminofuroxan (Via). A 25% solution of ammonia (200 ml) and chloroform (i00 ml) was added to IV (i g, 4.5 mmole) and refluxed with stirring for 2 h and cooled to 0~
The precipitated solid (0.6 g) was filtered off, transferred to a three necked flask, ether (50 ml) added, and a solution of KsFe(CN) 6 (1.66 g, 5 mmole) in ammonia solution (2%, 50 ml) added dropwise with stirring at 0~ over 15 min. Stirring was continued for 2 h at 0~ and a further i h at 200C. The ether layer was separated, washed with water and dried. After removal of ether the residue was chromatographed on a silica gel column using CCI~acetone (6:1).
4-(l-Adamantyl)-3-methylaminofuroxan (Vlb) was obtained similarly using a methylamine solution (33%, 60 ml) and compound IV (i g). LITERATURE CITED i. L.I. Khmel'nitkii, S. S. Novikov, and T. I. Godovikova, Chemistry of Furoxans. Reactions and Uses, Nauka, Moscow (1983), p. 259. 2.