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Optica Publishing Group
  • Applied Spectroscopy
  • Vol. 46,
  • Issue 10,
  • pp. 1483-1487
  • (1992)

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

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Abstract

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.

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