Properties of furoxans monosubstituted with adamantanes

✍ Scribed by M. I. Kalinina; I. K. Moiseev

• Book ID: 104781580
• Publisher: Springer US
• Year: 1988
• Tongue: English
• Weight: 356 KB
• Volume: 24
• Category: Article
• ISSN: 0009-3122
• DOI: 10.1007/bf00473336

✦ Synopsis

Furoxans monosubstituted with a series of adamantanes have been obtained by oxidation of anti-[l-(3-R-ademantyl)]-amphi~ Depending on the conditions 4-(l-adamantyl)furoxan is partially isomerized to 3-(l-adamantyl)furoxan or by increasing the time of boiling and concentration of furoxan in p-xylene is isomerized to the thermodynamically stable 3-(l-adamantyl)-l,2,4-oxadiazol-5-one. teristic of monosubstituted furoxans [3]: 3180-3150, 930 cm-I. OH R la-e As a continuation of our investigations into the chemical conversions of anti-[l-(3-Rademantyl)]-amphi-glyoximes (Ia-e) [i] we have studied the possibility of forming heterocycles from them. It was found that when glyoximes Ia-e are oxidized with 1.2 moles of nitric acid (d 1.5) in 60-80 moles of glacial acetic acid, ~-[l-(3-R-adamantyl)]furoxans (IIa-e) are readily formed. The use of 4 N or 8 N nitric acid [2] as oxidizing agent leads to a reduction in the rate of formation of furoxan IIa.

In the IR spectra of the compounds synthesized IIa-e there are several bands charac-