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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.
Inorganic Chemistry
|October 24, 2001
Summary
Two new one-pot synthesis methods efficiently produce nido-6-alkyldecaborane(14) compounds. These regioselective routes offer high yields for novel boron hydride derivatives.
Area of Science:
- Inorganic Chemistry
- Boron Hydride Chemistry
Background:
- Decaborane derivatives are important in various chemical applications.
- Existing synthesis routes for substituted nido-decaboranes can be complex and low-yielding.
- Development of efficient and regioselective synthetic methodologies is crucial.
Purpose of the Study:
- To report two novel, high-yield, one-pot synthetic routes to nido-6-alkyldecaborane(14)s.
- To characterize key intermediates and final products using X-ray diffraction.
Main Methods:
- Regioselective addition of alkyllithium reagents to nido-B(10)H(13)(-) followed by protonation.
- Olefin hydroboration of arachno-6,9-(SMe(2))(2)-B(10)H(12) followed by reduction and protonation.
- X-ray diffraction analysis of selected boron hydride intermediates and products.
Main Results:
- Successful synthesis of nido-6-alkyldecaborane(14)s via two distinct one-pot procedures.
- Characterization of intermediates such as arachno-6-R-B(10)H(13)(2)(-), arachno-6-R-B(10)H(14)(-), nido-6-R-8-(SMe(2))-B(10)H(11), and nido-6-R-B(10)H(12)(-).
- Structural confirmation of 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) via X-ray diffraction.
Conclusions:
- Two efficient and regioselective one-pot syntheses for nido-6-alkyldecaborane(14)s have been established.
- The reported methods provide access to valuable substituted boron hydride compounds.
- Structural data from X-ray diffraction enhance the understanding of these boron cage compounds.