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Kinetic control in the benzylidenation of some 1-alkylcyclohexane-cis-1,2-diols

✍ 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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✦ 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.


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