The chemistry of aryllead tricarboxylates. Synthesis of some α-aryl α,β-unsaturated carbonyl compounds

1983 ◽  
Vol 36 (2) ◽  
pp. 311 ◽  
Author(s):  
RP Kopinski ◽  
JT Pinhey
Keyword(s):  
Carbonyl Compounds ◽  
Methyl Substituent ◽  
Excellent Yield ◽  
Derivatives Of

The treatment of 4-benzoyltetrahydrofuran-2,3-dione (2a) with 2 equiv. of phenyllead triacetate (3a) in chloroform gives 1,2-diphenylpropenone (4a) in excellent yield. This reaction has been investigated with a number of similar derivatives of tetrahydrofuran-2,3-dione and a number of aryllead triacetates. It has been found to be very sensitive to the nature of the substituent at C4, and it would appear to be limited to the synthesis of a-methylene carbonyl compounds since a 5-methyl substituent inhibits the reaction.

Study of the structure and reactivity of nitrogen-containing derivatives of carbonyl compounds

1968 ◽  
Vol 17 (5) ◽  
pp. 940-944
Author(s):  
Yu. P. Kitaev ◽  
B. L. Moldaver ◽  
I. M. Skrebkova ◽  
V. G. Yakutovich
Keyword(s):  
Carbonyl Compounds ◽  
Derivatives Of

scholarly journals Synthesis and antitrypanosomal activities of a series of 7-deaza-5'-noraristeromycin derivatives with variations in the cyclopentyl ring substituents.

1997 ◽  
Vol 41 (8) ◽  
pp. 1658-1661 ◽  
Author(s):  
K L Seley ◽  
S W Schneller ◽  
D Rattendi ◽  
S Lane ◽  
C J Bacchi
Keyword(s):  
Methyl Substituent ◽  
Prototype Structure ◽  
Growth Activity ◽  
Derivatives Of ◽  
Related Compounds

Previous work in our laboratories has suggested that (+)-5'-nor-7-deazaaristeromycin (compound 1) may represent a prototype structure for a series of compounds with significant antitrypanosomal activities. To test this possibility, a series of derivatives of compound 1 with changes in the cyclopentyl substituents (compounds 3 to 10) have been studied. Although some growth activity was obtained with the L-like compound 5, related compounds 3 and 7 had little or no activity below 100 microM. D-like compounds 4 and 6 showed some activity at or below 100 microM, but the most interesting finding was that both the D- and L-like compounds having a methyl substituent on the 4' position were most active.

scholarly journals Nucleofugal behavior of a β-shielded α-cyanovinyl carbanion

2018 ◽  
Vol 14 ◽  
pp. 3018-3024
Author(s):  
Rudolf Knorr ◽  
Barbara Schmidt
Keyword(s):  
Michael Addition ◽  
Carbonyl Compounds ◽  
Room Temperature ◽  
Experimental Conditions ◽  
Metal Free ◽  
Metal Derivatives ◽  
Carbonyl Addition ◽  
Derivatives Of

Sterically well-shielded against unsolicited Michael addition and polymerization reactions, α-metalated α-(1,1,3,3-tetramethylindan-2-ylidene)acetonitriles added reversibly to three small aldehydes and two bulky ketones at room temperature. Experimental conditions were determined for transfer of the nucleofugal title carbanion unit between different carbonyl compounds. These readily occurring retro-additions via C–C(O) bond fission may also be used to generate different metal derivatives of the nucleofugal anions as equilibrium components. Fluoride-catalyzed, metal-free desilylation admitted carbonyl addition but blocked the retro-addition.

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