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Synthesis, Properties, and Crystal Structure of Silyl Nitronates (Silyl Esters of aci ‐Nitroalkanes): Towards the S N 2 Reaction Path with Retention of Configuration at Silicon
Author(s) -
Colvin Ernest W.,
Beck Albert K.,
Bastani Bahram,
Seebach Dieter,
Kai Yasushi,
Dunitz Jack D.
Publication year - 1980
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19800630320
Subject(s) - silylation , chemistry , silicon , crystal (programming language) , medicinal chemistry , crystallography , stereochemistry , organic chemistry , catalysis , computer science , programming language
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.