Potassium fluoride catalyzed reactions between malononitrile and α, β-unsaturated ketones

1970 ◽  
Vol 48 (19) ◽  
pp. 3064-3075 ◽  
Author(s):  
J. W. ApSimon ◽  
J. W. Hooper ◽  
B. A. Laishes
Keyword(s):  
Carbonyl Group ◽  
Structure Elucidation ◽  
Potassium Fluoride ◽  
Knoevenagel Reaction ◽  
Unsaturated Ketone ◽  
Unusual Structure ◽  
Unsaturated Ketones ◽  
Condensation Products ◽  
Intramolecular Condensation ◽  
Catalyzed Reactions

The preparation and structure elucidation of the condensation products between malononitrile and a variety of α,β-unsaturated ketones using potassium fluoride as catalyst is described. If the carbonyl group of the α,β-unsaturated ketone is hindered, then Michael addition occurs. If, however, the carbonyl group is unencumbered, a Knoevenagel reaction appears to occur first which, in many cases, is then followed by conjugate addition and intramolecular condensation to yield compounds of unusual structure.

Reactivity of [m]ferrocenophanones: The aldol condensation

1986 ◽  
Vol 51 (5) ◽  
pp. 1112-1118 ◽  
Author(s):  
Pavol Elečko ◽  
Štefan Toma ◽  
Miroslav Vrúbel ◽  
Eva Solčániová
Keyword(s):  
Carbonyl Group ◽  
Aldol Condensation ◽  
Basic Medium ◽  
Unsaturated Ketone ◽  
Cyclic Ketones ◽  
Unsaturated Ketones

Investigation of the reaction of [m]ferrocenophanones with p-chlorobenzaldehyde in basic medium showed that these cyclic ketones are much more reactive than their acyclic counterparts. The size of the bridge and the position of the carbonyl group influenced the reaction. Thus, [m]ferrocenophan-1-ones (m =3,4 afforded β-hydroxyketones only, [5]ferrocenophan-1-one gave in addition an α,β-unsaturated ketone, and [4]ferrocenophane-2-one yielded only α,β-unsaturated ketones. Oxidation of [m]ferrocenophanes with MnO2 furnished the expected monoketones and [4]ferrocenophane-1,4-dione and [5[ferrocenophane-1,2-dione. The preparation of [5]ferrocenophane-1,5-dione was also improved.

scholarly journals Synthesis of Galectin Inhibitors by Regioselective 3′-O-Sulfation of Vanillin Lactosides Obtained under Phase Transfer Catalysis

Molecules ◽  
2020 ◽  
Vol 26 (1) ◽  
pp. 115
Author(s):  
Karima Belkhadem ◽  
Yihong Cao ◽  
René Roy
Keyword(s):  
Carboxylic Acid ◽  
Sulfur Trioxide ◽  
Phase Transfer Catalysis ◽  
Phase Transfer ◽  
Aldehyde Group ◽  
Para Position ◽  
Knoevenagel Reaction ◽  
Aromatic Residue ◽  
Unsaturated Carboxylic Acid ◽  
Catalyzed Reactions

Vanillin-based lactoside derivatives were synthetized using phase-transfer catalyzed reactions from per-O-acetylated lactosyl bromide. The aldehyde group of the vanillin moiety was then modified to generate a series of related analogs having variable functionalities in the para- position of the aromatic residue. The corresponding unprotected lactosides, obtained by Zemplén transesterification, were regioselectively 3′-O-sulfated using tin chemistry activation followed by treatment with sulfur trioxide-trimethylamine complex (Men3N-SO3). Additional derivatives were also prepared from the vanillin’s aldehyde using a Knoevenagel reaction to provide extended α, β-unsaturated carboxylic acid which was next reduced to the saturated counterpart.

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