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

Research output: Contribution to journalArticlepeer-review

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.

Original languageEnglish (US)
Pages (from-to)2664-2673
Number of pages10
JournalACS Omega
Volume9
Issue number2
DOIs
StatePublished - Jan 16 2024
Externally publishedYes

Bibliographical note

Publisher Copyright:
© 2024 The Authors. Published by American Chemical Society.

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