Study on the enolization of alkylation of cis and trans 2-tert-5-X-1,3-dioxanes (X = CO2CH3, CHO, COPh, NO2, and CN). Evidence for stereoelectronic control

1 September 1986

journal article
Published by Canadian Science Publishing in Canadian Journal of Chemistry

Vol. 64 (9) , 1788-1794
https://doi.org/10.1139/v86-294

Abstract

Alkylation of 2-tert-butyl-5-X-1,3-dioxanes (X = CO₂CH₃, COPh, and NO₂) was studied. Products resulting from an equatorial approach of the alkylating agent are preferentially formed when X = CO₂CH₃ and NO₂. Also, the cis isomers that have an equatorial hydrogen at C-5 were found to deprotonate at a faster rate than the trans isomers when X = CO₂CH₃, COPh, CHO, and CN. These results are compared with those obtained with methyl 2-tert-butyl cyclohexane carboxylate and are interpreted by taking into account stereoelectronic principles.

Keywords

TRANS
ISOMERS
CHO
CIS
ALKYLATING
TERT BUTYL
DIOXANES
CO2CH3

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