Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 71, Issue 18, Pages 6851-6858Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo060968z
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- NIGMS NIH HHS [GM 61066] Funding Source: Medline
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Nucleophilic substitution reactions of 4-substituted cyclohexanone acetals display different selectivities depending upon the electronic nature of the substituent. Alkyl groups favor equatorial positions in the oxocarbenium ions, but alkoxy groups prefer axial conformers. The reactions of acetals with alkoxy groups constrained to either equatorial or axial positions suggest that the presence of an axial alkoxy group distorts the oxocarbenium ion, changing its inherent preferences for facial attack.
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