Dilithio 9,10-Diborataanthracene : Molecular Structure and 1,4-Addition Reactions


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LORBACH, Andreas, Michael BOLTE, Hans-Wolfram LERNER, Matthias WAGNER, 2010. Dilithio 9,10-Diborataanthracene : Molecular Structure and 1,4-Addition Reactions. In: Organometallics. 29(22), pp. 5762-5765. ISSN 0276-7333. eISSN 1520-6041. Available under: doi: 10.1021/om100825m

@article{Lorbach2010-11-22Dilit-39154, title={Dilithio 9,10-Diborataanthracene : Molecular Structure and 1,4-Addition Reactions}, year={2010}, doi={10.1021/om100825m}, number={22}, volume={29}, issn={0276-7333}, journal={Organometallics}, pages={5762--5765}, author={Lorbach, Andreas and Bolte, Michael and Lerner, Hans-Wolfram and Wagner, Matthias} }

9,10-Dihydro-9,10-diboraanthracene ([1]<sub>n</sub>) and its SMe<sub>2</sub> adduct 1(SMe<sub>2</sub>)<sub>2</sub> are readily reduced with lithium in THF to the dianionic 9,10-diborataanthracene Li<sub>2</sub>[1]. An X-ray crystal structure analysis of (Li(thf)<sub>2</sub>)<sub>2</sub>[1] revealed monomeric inverse sandwich complexes, each of them containing two Li(thf)<sub>2</sub> moieties coordinated to both sides of the central B<sub>2</sub>C<sub>4</sub> ring. Compared to 9,10-dimethyl-9,10-dihydro-9,10-diboraanthracene, the four B−C<sup>Ar</sup> bonds of (Li(thf)<sub>2</sub>)<sub>2</sub>[1] are shorter by 0.046(4) Å, thereby indicating an increased degree of B═C<sup>Ar</sup> double-bond character. Consequently, (Li(thf)<sub>2</sub>)<sub>2</sub>[1] reacts with 4,4′-dimethylbenzophenone as a B═C<sup>Ar</sup>−C<sup>Ar</sup>═B diene and undergoes a [4+2] cycloaddition reaction with formation of a bicyclic product. In contrast, tert-butylacetylene reacts with (Li(thf)<sub>2</sub>)<sub>2</sub>[1] under formal 1,4-addition of its methinic C−H group instead of its C≡C triple bond to the two boron atoms. Lerner, Hans-Wolfram Lerner, Hans-Wolfram Bolte, Michael 2017-06-07T09:48:41Z eng Wagner, Matthias Wagner, Matthias Dilithio 9,10-Diborataanthracene : Molecular Structure and 1,4-Addition Reactions Lorbach, Andreas Bolte, Michael 2010-11-22 Lorbach, Andreas 2017-06-07T09:48:41Z

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