Reactions of Et3ZnLi with Ketones: Electronic and Steric Effects1
- 25 October 2000
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 65 (23) , 7750-7756
- https://doi.org/10.1021/jo000630j
Abstract
Toluene solutions of composition Et3ZnLi react rapidly with aldehydes and ketones to form addition products. Et3ZnNa and Et3ZnK solutions react readily with the same substrates although metalation, as well as addition, is significant with substrates having α-hydrogens. The Et3ZnM solutions react with 2-cyclohexenone to give mainly the 1,4-addition product. Relative rates of addition of Et3ZnLi to substituted acetophenones give a Hammett ρ of 2.78. Addition of Et3ZnLi to acetophenone is slowed significantly by α and ortho methyl substituents; relative rates of addition to acetophenone, o-methylacetophenone, and tert-butyl phenyl ketone are 1.00, 0.012, and 0.003.Keywords
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