Synthesis, Properties, and Crystal Structure of Silyl Nitronates (Silyl Esters of <i>aci</i>‐Nitroalkanes): Towards the <i>S_N</i>2 Reaction Path with Retention of Configuration at Silicon

Abstract

Abstract An efficient and flexible method for the preparation of silyl nitronates is described (see 1–10 ). NMR. spectral investigations indicate a rapid 1,3‐silyl migration process, with an activation energy of about 10 kcal mol −1 . X‐ray crystallographic studies on the silyl nitronates 3 and 8 show structures that lean towards an S N 2 retention pathway at silicon.