Halogenation and nitrosation of 2-(1-adamantyl)indolizine

Abstract

Although 2-(1-adamantyl)indolizine (I) has long been known [1, 2], its chemical properties have not been studied so far. We performed reactions of compound I with bromine, sodium nitrite, and phosphorus(III) chloride. Comparison of the H NMR spectra of the products with those of methyl-substituted derivatives II and III [1] allowed us to assign structures IV and V to the bromination and nitrosation products, respectively. The reaction of I with PCl3 in sulfuric acid gave compound VI with chlorine atom in the adamantane fragment (cf. [3]).