4397-09-5Relevant articles and documents
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Klages,Haehn
, p. 1725 (1904)
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Highly efficient alkylation to ketones and aldimines with Grignard reagents catalyzed by zinc(II) chloride
Hatano, Manabu,Suzuki, Shinji,Ishihara, Kazuaki
, p. 9998 - 9999 (2007/10/03)
A highly efficient alkylation to ketones and aldimines with Grignard reagents in the presence of catalytic trialkylzinc(II) ate complexes derived from ZnCl2 (10 mol %) in situ was developed. This simple Zn(II)-catalyzed alkylation could minimize the well-known but serious problems with the use of only Grignard reagents, which leads to reduction and aldol side products, and the yield of desired alkylation products could be improved. Copyright
Reactions of Et3ZnLi with ketones: Electronic and steric effects
Musser,Richey Jr.
, p. 7750 - 7756 (2007/10/03)
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.