Kinetic control in the benzylidenation of some 1-alkylcyclohexane-cis-1,2-diols
β Scribed by Neil Baggett; Mohammed Mosihuzzaman; John M. Webber
- Publisher
- Elsevier Science
- Year
- 1985
- Tongue
- English
- Weight
- 616 KB
- Volume
- 136
- Category
- Article
- ISSN
- 0008-6215
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β¦ Synopsis
Acid-catalysed benzylidenation reactions of a series of alkyl substituted derivatives of cyclohexane-cis-1,2-diol have been studied. Preferential formation of the exe-phenyl benzyiidene acetal was observed in the initial kinetic phase of the reaction of the 1-tert-butyl derivative, whereas the e~~o-phenyl acetal was preferentially formed from other dials. This behaviour has been rationalised by consideration of the probable stabilities of conformations of the oxocarbonium ion intermediate.
π SIMILAR VOLUMES
Haloetherification reaction of the chiral ene acetals derived from unsaturated meso-1,2-diols and chiral non-racemic norbornene aldehyde proceeded in an intramolecular manner with an unexpectedly high kinetic control. This method has been successfully employed for the desymmetrization of unsaturated
Rate constants for base hydrolysis of the trzs-( 1,lO-phenanthroline)iron(II) cation and for solvolysis of the cis-dichlorobis(l,2-ethanediamine)cobalt(III~ cation have been measured in binary aqueous mixtures containing l,a-ethanediol, 1,2or 1,4-butanediol, 1,2-or 1,6-hexanediol, 1-propanol, or t-b