Synthesis and structure of benzoboroxoles: Novel organoboron heterocycles

Article abstract of DOI:10.1016/S0040-4039(99)01303-9

Benzoboroxoles (5) can be prepared from the readily available o-bromobenzyl alcohols via dilithiation followed by reaction with triisopropylborate. X-Ray structural analysis of 1-hydroxy-3(1H)-1,2-benzoboroxole (5a) as well as the results of ab initio molecular orbital calculations indicate a planar structure of the boron center with a relatively short C-B bond. Preliminary results regarding the chemistry of benzoboroxoles are also reported.