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GC/FT-IR Determination of the Relative Configuration of Spiro [2.n] Methylenecyclopropyl Carbinols Diastereoisomeric Pairs

Volume 46, Number 10 (Oct. 1992) Page 1483-1487

Afshari, M.; Guiliano, M.; Leandri, G.; Monti, H.


The reaction of 1-methylene-2-trimethylsilyl spiro[2.n] alkanes with aldehydes under almost neutral conditions using tetrabutylammonium fluoride is consistent with 80% of diastereoisomeric pairs of spiromethylene cyclopropyl carbinols. This study elucidates the stereochemistry of these alcohols using the GC/FT-IR technique for inseparable mixtures and FT-IR dilution technique for a separable pair.