206867-75-6Relevant academic research and scientific papers
A tricyclic N-pyrrolylborane with an exceptionally stable B-N bond
Wrackmeyer, Bernd,Schwarze, Bernd,Milius, Wolfgang,Boese, Roland,Parchment, Oswald G.,Webb, Graham A.
, p. 247 - 254 (1998)
Hydroboration of 2,5-diallylpyrrole by using a mixture diethylborane/triethylborane (Et2BH/Et3B) leads to the first tricyclic N-pyrrolylborane 3 which possesses an exceptionally stable B-N bond. In accordance with the pronounced Lewis-acidic character of 3, it is readily converted into adducts (6) or borates (9). The crystal structure of 3 was determined by X-ray analysis (triclinic, space group P1, Z=8) showing a fairly long B-N bond (mean value 144 pm), the first example of a diorgano N-pyrrolyl borane in which the pyrrole ring is not twisted against the C2BN-plane. Nuclear magnetic shielding (11B, 13C, 14N) was calculated using the GIAO procedure. BN(pp)π bonding is discussed on the basis of MO calculations.
