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2004
Intermediates
O 0190
Generation and Trapping of Cyclopropyldiazonium and Diazocyclopropane in the
of Cyclopropylamine with Alkyl Nitrites. — Cyclopropyldiazonium
52- 038 Nitrosation
ions (II), which are generated by reaction of cyclopropylamine (I) with alkyl nitrites,
can be easily trapped in azo-coupling reactions [→(IV), (VI)]. The presence of reactive
unsaturated compounds such as acrylate (VII) in the reaction mixture allows diazocyclopropane to be trapped under similar conditions in 1,3-dipolar cycloaddition reactions [→(VIII)]. This result along with deuterium exchange data suggest rapid interconversions of cyclopropyldiazonium ions and diazocyclopropane. — (TOMILOV*,
Y. V.; OKONNISHNIKOVA, G. P.; SHULISHOV, E. V.; NEFEDOV, O. M.; Russ.
Chem. Bull. 53 (2004) 3, 671-675; Zelinsky Inst. Org. Chem., Russ. Acad. Sci.,
Moscow 117913, Russia; Eng.) — R. Staver
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