PubMed · 5291221
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W T Reichle. 1971. Three coordinated complexes of copper(I).. https://doi.org/10.1111/j.1749-6632.1971.tb34952.x
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A bifunctional biaryl lactone has been synthesized that should be capable of iterative unidirectional aryl-aryl bond rotation via: (1) a diastereoselective lactone ring opening, (S)-1 to (P,S)-2 or (M,S)-2; (2) a chemoselective lactonization, (P,S)-2 or (M,S)-2 to (S)-3; and (3) a chemoselective hydrolysis, (S)-3 to (S)-1. Preliminary results of a racemic sample have indicated unidirectional 180 degrees rotation with very high directional selectivity per individual artificial molecular motor molecule through the first two steps of this sequence. [reaction: see text]
The reactivity of sodium borohydride in the presence of other species has been examined by adiabatic calorimetry. In combination with water, sodium borohydride exhibits an exotherm at room temperature accompanied by generation of gas (presumed to be hydrogen). Addition of potassium hydroxide to a sodium borohydride-water mixture is found to stabilize the solution and require a higher temperature for reaction to occur. However, if iron oxide is also included, reaction takes place near room temperature. Very rapid reaction was found when a metal chloride was brought in contact with a solution containing sodium borohydride, water, and potassium hydroxide. When sodium borohydride was added to an oxygenated hydrocarbon, reaction at room temperature also took place, but to a more limited extent. Peak temperatures above 200 degrees C and maximum pressures in excess of 2000 psia were observed in most cases. Kinetics extracted from the calorimetry data are presented for some of the sodium borohydride combinations.
A variety of N-tert-butanesulfinyl imines were reduced with NaBH4 in THF containing 2% water to provide the corresponding secondary sulfinamides in high yield and diastereoselectivity. By using the same sulfinyl imine starting materials and changing the reductant to L-Selectride, the stereoselectivity could be efficiently reversed to afford the opposite product diastereomer in high yield and selectivity.