α-naphthyl phenyl pinacols
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AbstractTreatment of α-naphthyl phenyl ketone with Zn/acetic acid gives racemic α-naphthyl phenyl pinacol [1,2-di(1-naphthyl)-1,2-diphenylethane-1,2-diol], C34H26O2, but reaction with Mg/MgI2 gives a product which proves to be not a pinacol, but a tricyclic compound (with four chiral centers, formed by addition at the 2-position of one of the naphthalene groups), racemic 5-(1-naphthyl)-3,5-diphenyl-4-oxatricyclo[7.4.0.0 2,6]trideca-7,9,11,13-tetraen-3-ol, C34H26O2. The aromatic ring in this tricyclic compound is planar, but the other six-membered ring, and the five-membered furano ring, are non-planar. Bond lengths and angles in both molecules correspond to the molecular formulations. In both structures, the OH groups are involved in only weak intermolecular interactions.
All Author(s) ListMak T.C.W., Patrick B.O., Rettig S.J., Scheffer J.R., Trotter J., Ukpabi P., Wu B.-M., Yee V.C.
Journal nameActa Crystallographica Section C: Crystal Structure Communications
Year1998
Month8
Day15
Volume Number54
Issue Number8
PublisherBlackwell Publishing Inc.
Place of PublicationUnited Kingdom
Pages1148 - 1151
ISSN0108-2701
eISSN1600-5759
LanguagesEnglish-United Kingdom
