15295-60-0Relevant articles and documents
Synthesis of acetals from alkenes by one-pot hydroformylation-transacetalization reactions catalysed by rhodium complexes and pyridinium p-toluenesulphonate
Fernandez, Elena,Castillon, Sergio
, p. 2361 - 2364 (1994)
Efficient conversion of alkenes to acetals has been achieved by consecutive hydroformylation-acetalization reactions catalyzed by rhodium complexes and pyridinium p-toluenesulphonate or by a zwitterionic rhodium catalyst.
On the Mechanism of Lewis Acid Mediated Nucleophilic Substitution Reactions of Acetals
Mori, Ichiro,Ishihara, Kazuaki,Flippin, Lee A.,Nozaki, Kyoko,Yamamoto, Hisashi,et al.
, p. 6107 - 6115 (2007/10/02)
Lewis acid mediated nucleophilic substitution of acetals can occur by direct displacement (SN2) or oxocarbenium ion (SN1) mechanisms.With acyclic acetals, stereoselectivity increases with increasing steric bulk of the alkoxy group and with increasing polarity of the reaction medium.The enhanced stereoselectivity observed with acetals of secondary and tertiary alcohols is explained by perturbation of the approach trajectory of the nucleophilic alkene as it attacks the oxocarbenium ion.Highest stereoselectivity is seen in the reaction of 2-(1-phenylethyl)-4,4,5,5-tetramethyl-1,3-dioxolane (4) with enol silane 5; only one diastereomeric product (9s) is obtained, even in the relatively nonpolar solvent CH2Cl2.The TiCl4-mediated reactions of cyclic acetals 18c, 18t, 25, and 28 with silyl enol ether 5 show that in these systems the substitution does not occur by the SN2 mechanism.
A Simple and Efficient Conversion of Aldehyde Acetals into Esters
Sugai, Saburo,Kodama, Takashi,Akaboshi, Sanya,Ikegami, Shiro
, p. 99 - 105 (2007/10/02)
The reaction of aldehydic acetals with hypochlorous acid in acetic acid-acetone afforded the corresponding esters in excellent yields.From cyclic acetals, only the corresponding hydroxyalkyl esters were obtained.Keywords - acetal; hypochlorite; hypochlorous acid; conversion; ester; hydroxyalkyl ester; regioselectivity