Synthesis and Conformational Studies of Tertiary Alcohols Derived from Tetrahydro-4H-pyran-4-one and Tetrahydrothiopyran-4-one

Kevin Tran, Kenneth Darrell Berlin, Elizabeth M. Holt, Randal L. Hallford, Margaret A. Eastman, V. К. Yu, Калдыбай Джайловович Пралиев

2005

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DOI 10.1080/104265090507641
Data confidence 70 medium
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Abstract

A series of derivatives of tetrahydro-4 H-pyran-4-one and tetrahydrothiopyran-4-one have been prepared by condensation with aryl Grignard reagents. IR spectra, 1 H and 13 C NMR spectral analyses, and elemental analyses support the structures. A single-crystal X-ray diffraction analysis of 4-(3,5-dimethylphenyl)tetrahydrothiopyran-4-ol [a = 9.729(10), b = 12.846(2), c = 9.970(10) Åi; space group Pna2(1)] confirmed the aryl group is located in a pseudo equatorial position, and the heterocyclic ring is slightly flattened near the sulfur end of the molecule.