Synthese von 12‐Cyano‐15‐hexadecanolid durch Ringerweiterung von 1‐(3′‐Hydroxybutyl)‐2‐oxocyclododecan‐1‐carbonitril
- 18 December 1985
- journal article
- research article
- Published by Wiley in Helvetica Chimica Acta
- Vol. 68 (8) , 2115-2118
- https://doi.org/10.1002/hlca.19850680804
Abstract
Synthesis of 12‐Cyano‐15‐hexadecanolide by Ring Enlargement of 1‐(3′‐Hydroxybutyl)‐2‐oxocyclododecane‐1‐carbonitrileIn the presence of Bu4NF, 2‐oxocyclododecane‐1‐carbonitrile (1) reacted with acrylaldehyde to form the corresponding aldehyde 2 which was methylated, e.g. with CH3 Ti[OCH(CH3)2]3. The resulting 1‐(3′‐hydroxybutyl)‐2‐oxocyclododecane‐1‐carbonitrile (5) was converted to 12‐cyano‐15‐hexadecanolide (6) in nearly quantitative yield under the influence of Bu4NF.Keywords
This publication has 6 references indexed in Scilit:
- Studies on the Carbon Zip Reaction of 2‐Oxocycloalkane‐1‐carbonitrilesHelvetica Chimica Acta, 1985
- Synthesen makrocyclischer Lactone durch Ringerweiterung Herstellung von (±)‐Phoracantholid I, (±)‐Dihydrorecifeiolid und (±)‐15‐HexadecanolidHelvetica Chimica Acta, 1984
- Organotitanium reagents in organic synthesis a simple means to adjust reactivity and selectivity of carbanionsPublished by Springer Nature ,1982
- Synthese von 3‐Oxo‐8‐oxabicyclo[3.2.1]oct‐6‐en‐2‐carbonitrilen aus γ‐Brom‐β‐oxonitrilen und Furan via [4 + 3]‐Cycloaddition von 1‐Cyanallylium‐2‐olatenEuropean Journal of Inorganic Chemistry, 1982
- The preparation and properties of some σ-alkyl and σ-aryl derivatives of titaniumJournal of Organometallic Chemistry, 1974
- Alkoxy‐methyl‐titanchlorideEuropean Journal of Organic Chemistry, 1968