1957
DOI: 10.1021/ja01570a037
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The Reaction of Acetals with Malonic Acid and its Derivatives. A Contribution to the Knowledge of the Knoevenagel-Doebner Reaction

Abstract: The acetals of aromatic aldehydes, cinnamic aldehydes and-with lower yields-also of aliphatic aldehydes react withThe reaction does not Ethyl hydrogen malonate reacts with these acetals analogously in the absence of any catal>Tst, -4 reaction mechanism is proposed, inmalonic acid in the presence of pyridine and piperidine in the manner of a Knoevenagel reaction. proceed via the free aldehydes.giving the corresponding ethyl hydrogen arylidene-and cinnamylidene-malonates. voking the formation of a hydrogen-bonde… Show more

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Cited by 45 publications
(14 citation statements)
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“…Easily available aromatic aldehydes diethyl acetals react with trimethylsilyl phosphites similarly but only under heating at 100‐150°C to give ethoxymethylphosphonates 3 in high yields. The synthesis of the phosphonate 3b proceeds only in the presence of a mixture of zinc chloride and cadmium iodide as catalysts.…”
Section: Resultsmentioning
confidence: 99%
See 1 more Smart Citation
“…Easily available aromatic aldehydes diethyl acetals react with trimethylsilyl phosphites similarly but only under heating at 100‐150°C to give ethoxymethylphosphonates 3 in high yields. The synthesis of the phosphonate 3b proceeds only in the presence of a mixture of zinc chloride and cadmium iodide as catalysts.…”
Section: Resultsmentioning
confidence: 99%
“…All reactions were carried out under dry argon in anhydrous solvents. The starting trimethylsilyl esters of trivalent phosphorus acids, aldehyde acetales, and substituted benzalchlorides were prepared as described below.…”
Section: Methodsmentioning
confidence: 99%
“…The dimethyl acetal 6 (5,6) and the protected cyanohydrin derivatives 8 and 9 (7-9) were readily prepared following standard '~uthor to whom correspondence may be addressed.…”
Section: H T Results and Discussionmentioning
confidence: 99%
“…Since many acetals and ketals are extremely susceptible to acid-catalyzed hydrolysis and dealcoholysis, the final work-up should be carried out under alkaline conditions, with the exclusion of moisture. A number of good general procedures for converting aldehydes and ketones to acetals and ketals by reaction with orthoformates and alcohols have been described in the literature (6,23,67,151,160,248,285).…”
Section: T a B L E Ii Equilibrium Constants For Conversion Of Ketonesmentioning
confidence: 99%
“…C 3 compounds: propionaldehyde (225), 2,2-dibromopropanal (67, 127, 151a, 187, 250, 255, 290), 2-fluoro-5-hydroxypropanal (156), acetone (9,11,59,64,67,69,107,137,143,190,220,223), chloroacetone (9), acetoxyacetone (102) 1,1-dichloroacetone (301), l-acetoxy-3-hydroxyacetone (8, 23a, 110), acrolein (111,231,247,285) (64,67,126,279), 5-ethoxyfurfural (109), 3methylthio-2-thiophenecarboxaldehyde (124b), and 2-selenophenecarboxaldehyde (217). C 6 compounds: 2-hexanone (11,101), 3,3-dimethyl-2-butanone (16,59,220), 6-formyloxyhexanal (4, 5), 2-methylcyclopentanone (5), cyclohexanone (12,151,178,190,215,248), 2-methyl-l-penten-3-one (8) (64,67,108,160,225), m-aminobenzaldehyde (42), m-and /?-nitrobenzaldehyde (108), /?-chlorobenzaldehyde (108), ο-, m-, and /7-hydroxybenzaldehyde (34,…”
Section: T a B L E Ii Equilibrium Constants For Conversion Of Ketonesmentioning
confidence: 99%