Journal article
Unsaturated nitriles: stereoselective MgO eliminations
Journal of organic chemistry, v 67(11), pp 3668-3672
31 May 2002
PMID: 12027678
Featured in Collection : UN Sustainable Development Goals @ Drexel
Abstract
Alpha,beta-unsaturated nitriles are readily synthesized by eliminating MgO from beta-hydroxynitriles. Deprotonating acyclic, and cyclic, beta-hydroxynitriles with excess MeMgCl smoothly generates dianion intermediates that eject MgO with concurrent formation of alpha,beta-unsaturated nitriles. Alternatively, sequential addition of lithioacetonitrile and MgBr(2) to aldehydes and ketones generates magnesium alkoxides in situ that eliminate MgO upon addition of MeMgCl. The MeMgCl-induced MgO eliminations smoothly generate alpha,beta-unsaturated nitriles from hindered ketones that are otherwise difficult to synthesize.
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Details
- Title
- Unsaturated nitriles: stereoselective MgO eliminations
- Creators
- Fraser F Fleming - Duquesne UniversityBrian C Shook - Duquesne University
- Publication Details
- Journal of organic chemistry, v 67(11), pp 3668-3672
- Publisher
- American Chemical Society; Washington, DC
- Resource Type
- Journal article
- Language
- English
- Academic Unit
- Chemistry
- Web of Science ID
- WOS:000175915000016
- Scopus ID
- 2-s2.0-0037204694
- Other Identifier
- 991020898499404721
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- Web of Science research areas
- Chemistry, Organic