Issue 0, 1967

The conformational analysis of saturated heterocycles. Part X. Steric requirements of the nitrogen lone pair from aza-cis-decalin equilibria

Abstract

The methoxide-catalysed equilibration of cis- and trans-1-methoxycarbonyl-cis-decalin has been studied over the range 25–106° in methanol and in glyme by gas chromatography. The equilibration of cis- and trans-4-methoxycarbonyl-1-methyl-1-aza-cis-decalin in methanol, n-propanol, glyme, and diglyme was studied at 25–85° by conductimetric analysis, and involved isolation of the cis-cis-derivative* by preferential reaction of its isomer with methyl iodide. The results were combined to show that in non-hydrogen-bonding solvents the conformer with the lone pair “inside” is considerably more stable than the other, whereas in hydrogen-bonding solvents there is little preference. The results are discussed in terms of the steric requirements of free and solvated lone pairs.

Article information

Article type
Paper

J. Chem. Soc. B, 1967, 487-492

The conformational analysis of saturated heterocycles. Part X. Steric requirements of the nitrogen lone pair from aza-cis-decalin equilibria

K. Brown, A. R. Katritzky and A. J. Waring, J. Chem. Soc. B, 1967, 487 DOI: 10.1039/J29670000487

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