Does the title compound prefer OLi or CLi contacts in the solid state? OLi contacts are characteristic of lithiated phenylsulfones, CLi contacts of allyllithium compounds. According to the X‐ray structure analysis, the chiral dimer 1 with OLi contacts is present in the crystal. The angle at C‐1 corresponds to a middle position between sp3 and sp2 hybridization. These results also hold for the structure of 1 in solution.
I This work was supported by the Deutsche Forschungsgemeinschaft and Angew Chem. Int. Ed. Engl. 24 (1985) No. 7 0 VCH Verlagsgesellschafi mbH, 0-6940 Weinheim. 1985 0570-0833/85/0707-0611 $ 02.50/0
Two new minor components of East Indian sandalwood oil have been isolated by chromatography. Structure elucidation using spectroscopical methods resulted in formulae 1 and 2. The relative configurations of the epimeric sesquiterpene aldehydes 1 , 2 were determined by two-dimensional NMR-analysis (HETCOR-, INADEQUATE-, and NOE-experiments) of the corresponding acids, cyclosantalic acid (3) and epicyclosantalic acid (4). The proposed structures of the aldehydes were confirmed by oxidative degradation reactions. Both aldehydes could be oxidized under normal conditions resulting in the known products acetyldihydroalbene (7) and albene (12) but also some new products such as the acids 3,4 and the formates 8,9. Trace amounts of those oxidation products could also be detected as constituents of sandalwood oil. A possible biogenetic pathway leading from p-santalane derivatives to the cyclosantalals is briefly discussed.
The first dilithioalkyl sulfone, the title compound 2, was obtained by stepwise lithiation of the trimethylsilyl sulfone 1 with nBuLi. Compounds such as 2 are of interst with respect to their structure and their synthetic potential, e.g., for the preparation of novel functionalized organometallic compounds.
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