The syntheses and properties of C-silylimines and their thermal rearrangements to N-silylenamines

Author:

Brook Adrian G.,Golino Carlo,Matern Eberhard

Abstract

C-Silylimines have been synthesized by silylation of lithioaldimines prepared from isonitriles. Their ultraviolet and C=N infrared absorptions show bathochromic shifts relative to related aldimines or ketimines and the nmr spectra show the presence of syn–anti isomers, probably due to nitrogen inversion. The silylimines undergo intramolecular thermal rearrangements at about 200–235 °C yielding N-silylenamines, which have been characterized.

Publisher

Canadian Science Publishing

Subject

Organic Chemistry,General Chemistry,Catalysis

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1. Efficient Synthesis of α-Tertiary α-Silylamines from Aryl Sulfonylimidates via One-Pot, Sequential C–Si/C–C Bond Formations;Organic Letters;2012-05-23

2. Silylmethylamines and their derivatives: Chemistry and biological activities;ADV ORGANOMET CHEM;2005

3. Silylmethylamines and Their Derivatives: Chemistry and Biological Activities;Advances in Organometallic Chemistry;2004

4. References to Volume 5;Comprehensive Organic Functional Group Transformations;1995

5. References to Volume 4;Comprehensive Organic Functional Group Transformations;1995

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