anti-Tricyclo[4.2.1.1^2,5]deca-3,7-diene-9-endo,10-endo-diol

Abstract

The title compound, C10H12O2, was synthesized as a candidate for further functionalization. The asymmetric unit comprises two independent molecules, both of which are situated on a center of symmetry. Both molecules are involved in a network of hydrogen bonding, with each alcohol group participating in one hydrogen bond as a donor and in a second hydrogen bond as an acceptor

anti-Tricyclo[4.2.1.12,5]deca-3,7-diene-9,10-dione

“…The title compound 4 is accessible through photoisomerization of Diels-Alder adduct 3, a transformation that has been thoroughly studied (Baggiolini et al, 1967;Klinsmann et al, 1972) since dione 4 -via diol 5 (Amman et al, 1980;Amman & Ganter, 1977;Amman & Ganter, 1981) -is a valuable precursor to an unusual bishomoaromatic dication (Prakash et al, 1987) and to heterodiamantanes and other oxa-cage compounds (Amman et al, 1980;Amman & Ganter, 1977;Amman & Ganter, 1981). We have recently reported the structure of diol derivative 5 (Harris et al, 2008) and herein report the structure of the parent dione 4.…”

“…For related structures, see: Eaton et al (2002); Harris et al (2008); Masters et al (1994). For the synthesis and related details, see: Hafner & Goliasch (1961); Weiss et al (1960); Dilthey & Quint (1930); Garbisch & Sprecher (1966); Saito & Ito (2008); Baggiolini et al (1967); Klinsmann et al (1972); Amman et al (1980); Amman & Ganter (1977, 1981; Prakash et al (1987); Harris et al (2008).…”

“…For related structures, see: Eaton et al (2002); Harris et al (2008); Masters et al (1994). For the synthesis and related details, see: Hafner & Goliasch (1961); Weiss et al (1960); Dilthey & Quint (1930); Garbisch & Sprecher (1966); Saito & Ito (2008); Baggiolini et al (1967); Klinsmann et al (1972); Amman et al (1980); Amman & Ganter (1977, 1981; Prakash et al (1987); Harris et al (2008). Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).…”

“…The synthesis of the title compound, 4, is described in our previous structure report (Harris et al, 2008). Crystals for data collection were obtained from a chloroform solution.…”