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
Keyword(s):
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.
2008 ◽
Vol 63
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pp. 1149-1154
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1994 ◽
Vol 49
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pp. 1818-1826
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1984 ◽
Vol 40
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pp. 816-818
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1964 ◽
Vol 239
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pp. 2482-2488
2018 ◽
Vol 28
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pp. 76-78
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