TY - JOUR
T1 - Nonclassical Stabilization of Planar Allenes
T2 - Low Rotational Barriers for Allene Double Bonds
AU - Steiner, Dirk
AU - Winkler, Heinz‐Jürgen ‐J
AU - Wočadlo, Sigrid
AU - Fau, Stefan
AU - Massa, Werner
AU - Frenking, Gernot
AU - Berndt, Armin
PY - 1994/11/2
Y1 - 1994/11/2
N2 - ππ and πσ delocalization facilitates rotation about the CC double bond adjacent to the boron atoms in 1. After rotation by 90° to the transition states, the negative charge of the highly polarized CCB2 bond is stabilized homoaromatically in a homodiboriranide, and the positive charge by hyperconjugation in a 3c2e bond. The energy difference between the planar transition state and orthogonal 1 is only 8.6 kcalmol−1. (Figure Presented.)
AB - ππ and πσ delocalization facilitates rotation about the CC double bond adjacent to the boron atoms in 1. After rotation by 90° to the transition states, the negative charge of the highly polarized CCB2 bond is stabilized homoaromatically in a homodiboriranide, and the positive charge by hyperconjugation in a 3c2e bond. The energy difference between the planar transition state and orthogonal 1 is only 8.6 kcalmol−1. (Figure Presented.)
UR - http://www.scopus.com/inward/record.url?scp=33748231861&partnerID=8YFLogxK
U2 - 10.1002/anie.199420641
DO - 10.1002/anie.199420641
M3 - 文章
AN - SCOPUS:33748231861
SN - 1433-7851
VL - 33
SP - 2064
EP - 2067
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
IS - 20
ER -