EVALUATION OF THE AROMATICITY OF BOREPIN - SYNTHESIS AND PROPERTIES OF 1-SUBSTITUTED BOREPINS

The reaction of 1,1-dibutylstannepin with BCl3 gave 1-chloroborepin, w hich has been converted to a variety of 1-substituted borepins, C6H6BX , where X = OH, O1/2, OCH3, 2,4,6-Me3C6H2, CH2CH2CH2NMe2, F, NH2, N(CH 2)5, N(iPr)2, H. 1-Chloroborepin and 1-aminoborepin have been investig ated by ab initio methods. All borepins have been studied using H-1 NM R, B-11 NMR, and C-13 NMR spectroscopy. The X-ray crystal structure of 1-chloroborepin gives evidence of a pi-delocalized structure. All pro perties are discussed in terms of the aromatic character of the borepi n ring system.