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A new bicyclic sulfonamide derivative, N-(1-(bromomethyl)-7,7-dimethylbicyclo[2.2.1]heptan-2-yl)benzenesulfonamide, was synthesized in the reaction of benzenesulfonamide and camphene in the presence of N-bromosuccinimide in acetonitrile. The proposed mechanism of investigated reaction involves the Wagner–Meerwein rearrangement stage. 3-(Bromomethylene)-2,2-dimethylbicyclo[2.2.1]heptane was isolated as a minor product. The products were characterized by IR, NMR spectroscopy, X-ray diffraction analysis, HRMS and elemental analysis data.

Comparative analysis of halotriflamidation of linear and cyclic dienes and trienes in different oxidative systems revealed a large variety of reactivity patterns. With linear dienes the haloamidation or solvent (MeCN) interception products or the products of their further transformations are formed. The NBSinduced reactions of conjugated cyclic dienes (cyclopentadiene, 1,3-cyclohexadiene, 1,3-cyclooctadiene) regioselectively afford bromoamidines at only one double bond with solvent interception. Dicyclopentadiene also gives bromamidine at the bicycloheptene double bond. With linear 5-methylhepta-1,3,6triene, 1,4-conjugate addition occurs with solvent interception and the halogen atom directed to the terminal olefinic carbon. Cyclododeca-1,5,9-triene reacts with triflamide differently depending on the oxidant to give amidine or azabicyclo[8.2.1]tridec-5-ene structure. The synthesized bromoamidines were converted into the corresponding imidazolines in close to quantitative yield.

Allyl halides with triflamide under oxidative conditions form halogen-substituted amidines. Allyl cyanide reacts with triflamide in acetonitrile or THF solutions in the presence of NBS to give the products of bromotriflamidation with a solvent interception, whereas in CH2Cl2 two regioisomers of the bromotriflamidation product without a solvent interception were obtained. The formed products undergo base-induced dehydrobromination to give linear isomers with the new C=C bond conjugated either with the nitrile group or the amidine moiety or alkoxy group. Under the same conditions, the reaction of allyl alcohol with triflamide gives rise to amidine, which was prepared earlier by the reaction of diallyl formal with triflamide. Unlike their iodo-substituted analogs, bromo-substituted amidines successfully transform into imidazolidines under the action of potassium carbonate.