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 | Zendy

Colvin Ernest W. | Zendy; Beck Albert K. | Zendy; Bastani Bahram | Zendy; Seebach Dieter | Zendy; Kai Yasushi | Zendy; Dunitz Jack D. | Zendy

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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.

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