The Synthesis of β,γ‐ and α,β‐Unsaturated Aldehydes via Polyene Epoxides
- 17 September 1980
- journal article
- research article
- Published by Wiley in Helvetica Chimica Acta
- Vol. 63 (6) , 1665-1674
- https://doi.org/10.1002/hlca.19800630636
Abstract
A substitute for the Darzens glycidic ester synthesis for converting unsaturated ketones or aldehydes into the homologated β,γ‐ or α,β‐unsaturated aldehydes employing sulfur ylides is described. The carbonyl group is converted into the unsaturated oxirane which is then rearranged to the new aldehyde. High yields of isomerically pure aldehydes are available by this method and the process is of practical importance in the conversion of β‐ionone into the β‐C14‐aldehyde, a key intermediate in the Isler synthesis of vitamin A. The efficient preparation of α‐ and β‐cyclocitral by the novel process is also described.This publication has 28 references indexed in Scilit:
- A Convenient Method for a Preparation of OxiranesHETEROCYCLES, 1977
- Enantioselective oxirane synthesis by means of dimethylsulfonium methylide and chiral phase-transfer catalystsJournal of the American Chemical Society, 1975
- Photochemistry of non-conjugated dienones. Part IV. Photolysis and thermolysis of some retro-α-ionones and retro-α-ionolsJournal of the Chemical Society, Perkin Transactions 2, 1974
- Development of a Laboratory-Scale Reciprocating Plate Extraction ColumnIndustrial & Engineering Chemistry Process Design and Development, 1972
- Synthesis of oxiranes from aqueous solutions of simple alkyl, allyl, and benzylsulfonium saltsThe Journal of Organic Chemistry, 1969
- Mechanism of the reaction of aqueous benzyldimethylsulfonium chloride and formaldehyde with sodium hydroxideJournal of the American Chemical Society, 1967
- Über eine neuartige Synthese von β‐Ketoallenen durch Reaktion von tertiären Acetylencarbinolen mit Vinyläthern eine ergiebige methode zur darstellung des Pseudojonons und verwandter verbindungenHelvetica Chimica Acta, 1967
- Dimethyloxosulfonium Methylide ((CH3)2SOCH2) and Dimethylsulfonium Methylide ((CH3)2SCH2). Formation and Application to Organic SynthesisJournal of the American Chemical Society, 1965
- Synthesis of Products Related to Vitamin A. IV. The Application of the Darzens Reaction to β-Ionone1aJournal of the American Chemical Society, 1948
- Sulfur Studies. XVI. The Synthesis of Certain Higher Alkyl Sulfonium Salts and Related CompoundsJournal of the American Chemical Society, 1940