Tetrahedron p. 1593 - 1598 (1980)
Update date:2022-07-31
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The addition of allyl and butenyl Grignard reagents to 4-t-butylcyclohexanone affords a greater proportion of the equatorial alcohols than is formed from the corresponding saturated Grignard reagents (propyl and s-butyl). In the case of the allyl Grignard reagent, the equatorial alcohol is the major product. Lithium aluminium hydride reduction in ether at 0° of cis and trans 4-t-butyl-2-methyl-cyclohexanone and cis and trans 4-t-butyl-2-chlorocyclohexanone affords mixtures of epimeric alcohols in ratios of equatorial to axial OH 8.4:1, 20:1, 4.2:1, and >70:1 respectively. These results fit in well with the view that polar interactions and torsional strain are both important in determining the steric course of the reaction.
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(2019)
