Preparation and X-ray Structural Study of Dibenzobromolium and Dibenzochlorolium Derivatives

Christopher D Huss; Akira Yoshimura; Gregory T Rohde; Irina A Mironova; Pavel S Postnikov; Mekhman S Yusubov; Akio Saito; Viktor V Zhdankin

doi:10.1021/acsomega.3c07512

Preparation and X-ray Structural Study of Dibenzobromolium and Dibenzochlorolium Derivatives

ACS Omega. 2024 Jan 3;9(2):2664-2673. doi: 10.1021/acsomega.3c07512. eCollection 2024 Jan 16.

Authors

Christopher D Huss¹, Akira Yoshimura^{1

2}, Gregory T Rohde³, Irina A Mironova⁴, Pavel S Postnikov^{4

5}, Mekhman S Yusubov⁴, Akio Saito⁶, Viktor V Zhdankin¹

Affiliations

¹ Department of Chemistry and Biochemistry, University of Minnesota Duluth, Duluth, Minnesota 55812, United States.
² Faculty of Pharmaceutical Sciences, Aomori University, 2-3-1 Kobata, Aomori 030-0943, Japan.
³ Marshall School, Duluth, Minnesota 55811, United States.
⁴ Research School of Chemistry and Applied Biomedical Sciences, The Tomsk Polytechnic University, Tomsk 634050, Russia.
⁵ Department of Solid-State Engineering, University of Chemistry and Technology, Prague 16628, Czech Republic.
⁶ Division of Applied Chemistry, Institute of Engineering, Tokyo University of Agriculture and Technology, 2-23-16 Naka-cho, Koganei, Tokyo 184-8588, Japan.

Abstract

Various five-membered cyclic dibenzobromolium salts (dibenzo[b,d]bromol-5-ium chloride, nitrate, hydrogen sulfate, dihydrogen phosphate, trifluoroacetate, and tetrafluoroborate) were prepared by diazotization-cyclization of 2'-bromo-[1,1'-biphenyl]-2-amine in solution of appropriate acids. The chlorolium analogues (iodide, trifluoroacetate, and tetrafluoroborate) were obtained by a similar procedure. Additional dibenzohalolium derivatives (dibenzo[b,d]bromol-5-ium and dibenzo[b,d]chlorol-5-ium azides, bis(trifluoromethanesulfonyl)imidates, thiocyanates, and trifluoromethanesulfonates) were prepared by anion exchange. Structures of ten of these dibenzohalolium derivatives were established by X-ray analysis. Bond distances and angles for the halogen atoms in different dibenzohalolium derivatives were summarized and discussed.