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Direct alkylation of α,β - unsaturated aldehydes

✍ Scribed by S.A.G. de Graaf; P.E.R. Oosterhoff; A. van der Gen

Publisher
Elsevier Science
Year
1974
Tongue
French
Weight
181 KB
Volume
15
Category
Article
ISSN
0040-4039

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✦ Synopsis

Alkylation of aldehydes, as a rule. requires transformation into intermediates such as enamines, to prevent base-catalysed condensations'. Only recently a direct alkylation with the aid of a phase-transfer catalyst, of aldehydes with a single a-hydrogen atom, was describedL. To our knowledge, the direct alkylation of the less-stable a,&unsaturated aldehydes has not been reported. Kloosterziel and coworkers studied anions of ketones and a.B-unsaturated aldehydes3. The anions were obtained by removing a proton from the substrate at low temperatures with potassium amide in liquid ammonia, and proved to be sufficiently stable to study their NMR-spec-tra3'4. We found, that this remarkable stability could serve as the basis for a simple, direct alkylation of a-substituted a,B-unsaturated aldehydes5. Both I-cyclohexene-I-carbaldehyde [h16

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Facile synthesis of β-alkyl-substituted
Facile synthesis of β-alkyl-substituted esters from α,β-unsaturated aldehydes
✍ Tsujiaki Hata; Masashi Nakajima; Mitsuo Sekine 📂 Article 📅 1979 🏛 Elsevier Science 🌐 French ⚖ 210 KB

8-Alkyl-substituted carboxylates were synthesized in good yields from U,B-unsaturated aldehydes by using the 1:l carbonyl adducts with diethyl bis(trimethylsily1) phosphite. Recently, several studies on acyl anion equivalents utilizing carbonyl insertion reactions have appeared. 2 It has been report