Benchtop-Stable Hypervalent Bromine(III) Compounds: Versatile Strategy and Platform for Air- and Moisture-Stable λ<sup>3</sup>-Bromanes
Kazunori Miyamoto, Motomichi Saito, Shunsuke Tsuji, Taisei Takagi, Motoo Shiro, Masanobu Uchiyama, Masahito Ochiai
Abstract
We present the first synthesis of air/moisture-stable λ3-bromanes (9 and 10) by using a cyclic 1,2-benzbromoxol-3-one (BBX) strategy. X-ray crystallography and NMR and IR spectroscopy of N-triflylimino-λ3-bromane (12) revealed that the bromine(III) center is effectively stabilized by intramolecular R–Br–O hypervalent bonding. This strategy enables the synthesis of a variety of air-, moisture-, and benchtop-stable Br-hydroxy, -acetoxy, -alkynyl, -aryl, and bis[(trifluoromethyl)sulfonyl]methylide λ3-bromane derivatives.
Topics & Concepts
Hypervalent moleculeChemistryIntramolecular forceBromineMoistureTrifluoromethylIntermolecular forceNuclear magnetic resonance spectroscopyArylOrganic chemistryPolymer chemistryAlkylIodineMoleculeOxidative Organic Chemistry ReactionsSynthesis and Catalytic ReactionsMarine Toxins and Detection Methods