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Optically active Fecht acid has been used for the preparation of a number of other optically active 2,6-disubstituted spiro[3.3]heptane derivatives. Application of Lowe's rule to the spiro[3.3]heptane system suggests the R configuration for the d-spiro [3.3] heptane-2,6-dicarboxylic acid. The optical purity of a few compounds could be determined. A discussion is given on the magnitude of the optical activity of 2,6-disubstituted spiro-[3.3]heptanes, as compared to the optical activity of dissymmetrical alienes. The low optical activity of the 2,6disubstituted spiro[3.3]heptane system gives rise to many exceptions to Lowe's rule, since other effects easily play a role in the optical activity. This is illustrated by carbonyl compounds, among which the Fecht acid (1), many of which show a sign of rotation opposite to the one expected on the basis of Lowe's rule.

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organic chemistry, review organic chemistry, review Z 0200 50 -294 Controlled Racemization of Optically Active Organic Compounds: Prospects for Asymmetric Transformation -(above 400 refs.). -(EBBERS, E. J.; ARIAANS, G. J. A.; HOUBIERS, J. P. M.; BRUGGINK, A.; ZWANENBURG, B.; Tetrahedron 53 (1997) 28, 9417-9476; Dep. Org. Chem., Cathol. Univ., NL-6525 ED Nijmegen, Neth.; EN)