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Antiaromaticity to Aromaticity: From Boroles to 1,2‐Azaborinines by Ring Expansion with Azides
Author(s) -
Braunschweig Holger,
Hörl Christian,
Mailänder Lisa,
Radacki Krzysztof,
Wahler Johannes
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201403101
Subject(s) - antiaromaticity , aromaticity , reactivity (psychology) , ring (chemistry) , chemistry , aryl , computational chemistry , combinatorial chemistry , crystallography , organic chemistry , molecule , medicine , alkyl , alternative medicine , pathology
Abstract We have exploited the reactivity of antiaromatic boroles, gaining access to aryl‐substituted monocyclic 1,2‐azaborinines. The observed ring‐expansion reaction of inherently electron‐deficient boroles with organometallic and organic azides is demonstrated for representative examples. This substance class is expected to provide a new avenue into 1,2‐azaborinine chemistry, especially in the area of functional organoboron materials. Our results are based on NMR and UV/Vis spectroscopy as well as single‐crystal X‐ray crystallography and provide a virtually quantitative approach that also offers numerous points of variation.