87034-00-2Relevant academic research and scientific papers
A General Method for the Preparation of γ-Substituted Cyclohexenals and Cycloheptenals
Jones, Tood K.,Denmark, Scott E.
, p. 4037 - 4045 (2007/10/02)
A general procedure for the preparation of γ-substituted or β'-unsaturated cycloalkenals is described.Starting from 2-cycloalkenones substituents may be introduced as nucleophiles by 1,4-addition followed by trapping of the regiospecifically generated enolate (86-92percent).Peracid oxidation of the enol silane derivative produces an α-hydroxy ketone which, after protection (70-93percent), is homologated to an enol ether by a Horner-Wittig reaction.Mild hydrolysis of the labile vinylogous acetal produces the aldehydes in good yields (62-75percent).Advantages of this method in comparison to known procedures are discussed as are other unsuccessful approaches to this substitution pattern.
CHEMISTRY OF ENOL ETHERS. 64. CONDENSATION OF ALICYCLIC SILYLDIENOL ETHERS WITH ORTHOFORMATES AND PENTENEDIAL ACETALS. SYNTHESIS OF 1,5- AND 1,9-DIALDEHYDE DERIVATIVES
Makin, S. M.,Kruglikova, R. I.,Tagirov, T. K.,Kolobova, T. P.
, p. 1044 - 1048 (2007/10/02)
1-Trimethylsilyloxy-2,4-polymethylene-1,3-butadienes were synthesized by reacting 1-formyl-1-cycloalkenes with trimethylchlorosilane and triethylamine.Their condensation with ethyl orthoformate led to the formation of alicyclic pentenedial monoacetals, wh
