Received 6 November 2012
In the title compound, C23H38O5, the oxabicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride unit has a normal geometry and the tetradecoxymethyl side chain is fully extended. In the crystal, molecules are linked head-to-head by C-HO hydrogen bonds, forming two-dimensional networks propagating along the a and c-axis directions.
Olefinic hydrogenation of an oxabicyclo[2.2.1]hept-5-ene derivative using catalytic quantities of 10% Pd on carbon as catalyst afforded the title compound. For reviews on the Diels-Alder reaction, see: Oppolzer (1991); Pindur et al. (1993). For a review on asymmetric cycloaddion processes, see: Pellissier (2012). For a review on catalytic hydrogenations, see: Brieger & Nestrick (1974). For a review on asymmetric catalytic hydrogenation processes, see: Knowles (2002). For discussions on reaction mechanisms with specifics on kinetic and thermodynamic control, see: Lowry & Richardson (1987); Smith (2012). For a discussion on Diels-Alder selectivity using maleic anhydride, see: Palmer (2004).
Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: publCIF (Westrip, 2010).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZL2516 ).
The authors gratefully acknowledge the National Science Foundation (NSF-CAREER grant to RES, CHE-0846680; NSF-RUI grant to DCF, CHE-0957482). DCF also gratefully acknowledges the Camille and Henry Dreyfus Foundation (TH-06-008) for partial support of this work.
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