Electronic absorption spectra of spiroborates and of 1,3,2-dioxaborinium salts

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Abstract

The preparation and spectra of tropophenylene spiroborates (III), 1,3-diketonato-benzodioxaborole (XVII), 1,3-diketonato-diphenylborine (XVIII), bis-1,3-diketonato-boronium salts (XIX) and 1,3,2-benzodioxaborinium salts (XX) are discussed. Interconversions between the last three classes of compounds are reviewed.

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      The bicyclic borates have perpendicular π-systems through four bonds of B–O. That‘s why researchers pay much attention to the issues of distribution of the electron density, the charge transfer, and, as a result of this effects, the change of the aromatic characteristics of the ligands. The literature contains rather detailed information on UV, NMR and IR spectroscopy for some spiro-borates [5,10–12], as well as X-ray diffraction of some of their representatives [13]. β-Diketones have a high complexing ability [14], and are used in the synthesis of dyes, phosphors, and for the extraction processes of heavy metals.

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      On replacing an –RCCR– bond in pyrylium cations by an –RBO– bond, one should obtain boroxaropyrylium (1,3,2-dioxaborinium) cations. The crystalline perchlorates (64TL2721, 65TL3917, 65TL3925, 67SA1373, 68T2499), revealed by X-ray diffractometry, however, an unexpected feature, namely one of the perchlorate oxygens is attached covalently to the diazaborinium cation resulting in a neutral system (83ZNA1161, 06ZNA360). The first six-membered aromatic heterocycles containing one boron atom together with a second heteroatom (oxygen or nitrogen, namely boroxaro- and borazaro-derivatives, respectively) were prepared by Dewar and Pettit in 1955–1956 (55CIL199, 56JCS2021, 56JCS2026).

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    Paper presented at the 8th European Congress on Molecular Spectroscopy, Copenhagen, 17 August 1965.

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