Structure and Natural Bond Orbital Analysis of Oxiranes Substituted with a Group 14 Element. A Comment of S_N2 Regioselectivity
Crystal structure analysis of oxiranes substituted with a group 14 element revealed that silyl and stannyl groups lengthened their α C–O bonds. Natural bond orbital analysis showed that silyl group raised the energy level of α C–O σ orbital and lowered that of α C–O σ<SUP>*</SUP> orbital. It was suggested that the former might lengthen the α C–O bond and that the latter should affect the regioselectivity in ring-opening reactions.
- Chemistry letters
Chemistry letters 1999(5), 409-410, 1999-05-05
The Chemical Society of Japan