Reactions involving electron transfer. III. Conjugate addition of lithium dimethylcuprate to .alpha.,.beta.-unsaturated carbonyl compounds

1972 ◽  
Vol 94 (15) ◽  
pp. 5495-5497 ◽  
Author(s):  
Herbert O. House ◽  
Michael J. Umen
Keyword(s):  
Electron Transfer ◽  
Carbonyl Compounds ◽  
Conjugate Addition ◽  
Alpha Beta

Conjugate addition of carbene anions to .alpha.,.beta.-unsaturated carbonyl compounds

1977 ◽  
Vol 16 (12) ◽  
pp. 3059-3063 ◽  
Author(s):  
Charles P. Casey ◽  
William R. Brunsvold ◽  
Daniel M. Scheck
Keyword(s):  
Carbonyl Compounds ◽  
Conjugate Addition ◽  
Alpha Beta

scholarly journals Hypervalent iodine oxidation of .ALPHA.,.BETA.-unsaturated carbonyl compounds.

1987 ◽  
Vol 35 (2) ◽  
pp. 570-577 ◽  
Author(s):  
YASUMITSU TAMURA ◽  
TAKAYUKI YAKURA ◽  
HIROAKI TERASHI ◽  
JUN-ICHI HARUTA ◽  
YASUYUKI KITA
Keyword(s):  
Carbonyl Compounds ◽  
Hypervalent Iodine ◽  
Alpha Beta

Organic reactions using sodium hydrogentelluride. 3. The Reaction of Sodium Hydrogentelluride with .alpha.,.beta.-Unsaturated Carbonyl Compounds

1994 ◽  
Vol 59 (12) ◽  
pp. 3500-3502 ◽  
Author(s):  
Masakazu Yamashita ◽  
Yoshifumi Tanaka ◽  
Akishi Arita ◽  
Minoru Nishida
Keyword(s):  
Carbonyl Compounds ◽  
Organic Reactions ◽  
Alpha Beta

Studies on electrooxidation of lignin and lignin model compounds. Part 1: Direct electrooxidation of non-phenolic lignin model compounds

Holzforschung ◽  
2012 ◽  
Vol 66 (3) ◽  
Author(s):  
Takumi Shiraishi ◽  
Toshiyuki Takano ◽  
Hiroshi Kamitakahara ◽  
Fumiaki Nakatsubo
Keyword(s):  
Electron Transfer ◽  
Cyclic Voltammetry ◽  
Carbonyl Compounds ◽  
Model Compounds ◽  
Lignin Model Compounds ◽  
Bulk Electrolysis ◽  
Lignin Model ◽  
Dimeric Compound ◽  
High Yields ◽  
Short Time

Abstract The direct anodic oxidation of non-phenolic lignin model compounds was investigated to understand their basic behaviors. The results of cyclic voltammetry (CV) studies of monomeric model, such as 1-(4-ethoxy-3-methoxyphenyl)ethanol, are interpreted as the oxidation for Cα-carbonylation did not proceed in the reaction without a catalyst, but a base promotes this reaction. Indeed, the bulk electrolyses of the monomeric lignin model compounds with 2,6-lutidine afforded the corresponding Cα-carbonyl compounds in high yields (60–80%). It is suggested that deprotonation at Cα-H in the ECEC mechanism (E=electron transfer and C=chemical step) is important for Cα-carbonylation. In the uncatalyzed bulk electrolysis of a β-O-4 model dimeric compound, 4-ethoxy-3-methoxyphenylglycerol-β-guaiacyl ether, the corresponding Cα-carbonyl compound was not detected but as a result of Cα-Cβcleavage 4-O-ethylvanillin was found in 40% yield. In the electrolysis reaction in the presence of 2,6-lutidine (as a sterically hindered light base), the reaction stopped for a short time unexpectedly. These results indicate the different electrochemical behavior of simple monomeric model compounds and dimeric β-O-4 models. The conclusion is that direct electrooxidation is unsuitable for Cα-carbonylation of lignin.

Conjugate addition of dimethylphenylsilyllithium to α,β-unsaturated carbonyl compounds mediated by sub-stoichiometric quantities of dimethylzinc

1997 ◽  
Vol 38 (42) ◽  
pp. 7313-7316 ◽  
Author(s):  
Bonnie L. MacLean ◽  
Kimberlea A. Hennigar ◽  
Kevin W. Kells ◽  
Robert D. Singer
Keyword(s):  
Carbonyl Compounds ◽  
Conjugate Addition
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