Molbank (May 2023)

Synthesis and Structure of <i>N</i>-(1-(Bromomethyl)-7,7-dimethylbicyclo[2.2.1]heptan-2-yl)benzenesulfonamide

  • Ivan A. Garagan,
  • Mikhail Yu. Moskalik,
  • Irina V. Sterkhova,
  • Anton S. Ganin

DOI
https://doi.org/10.3390/M1645
Journal volume & issue
Vol. 2023, no. 2
p. M1645

Abstract

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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.

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