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Monoalkyldecaborane(14) Syntheses via Nucleophilic Alkylation and Hydroboration
Adam N. Bridges1, Douglas R. Powell, Joel A. Dopke
1Department of Chemistry, University of Wisconsin-Madison, Madison, Wisconsin 53706.
Abstract:
Two regioselective, high-yield routes to nido-6-alkyldecaborane(14)s via one-pot syntheses are reported. Alkyllithium reagents add to salts of nido-B(10)H(13)(-) to form arachno-6-R-B(10)H(13)(2)(-), which may be protonated using HCl/Et(2)O, first to the corresponding arachno-6-R-B(10)H(14)(-) anion and then, with H(2) loss, to nido-6-R-B(10)H(13). Alternately, olefin hydroboration of arachno-6,9-(SMe(2))(2)-B(10)H(12) produces nido-6-R-8-(SMe(2))-B(10)H(11), which may be reduced, using Superhydrid, to nido-6-R-B(10)H(12)(-), and then protonated with HCl/Et(2)O to nido-6-R-B(10)H(13). X-ray diffraction studies of the following intermediates and products are presented: nido-8-(SMe(2))-B(10)H(12), nido-6-Thx-8-(SMe(2))-B(10)H(11), and nido-6-Thx-B(10)H(13).
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