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Physical Data: d204 = 0.801 g cm-3.
Solubility: sol dichloromethane, benzene, toluene, xylene, hexane, diethyl ether, diglyme, DME, and ethyl acetate; insol but reacts slowly with water; reacts with alcohols, acetone.
Form Supplied in: neat complex, colorless liquid, ca. 10 M in BH3; contains slight excess of dimethyl sulfide.
Preparative Method: Diborane generated by the reaction of Sodium Borohydride with Boron Trifluoride Etherate in diglyme3 is absorbed in Dimethyl Sulfide.
Handling, Storage, and Precautions: use in a fume hood; flammable liquid with stench; reacts with atmospheric moisture forming a crust of boric acid. Store and handle under nitrogen or argon. Stable indefinitely when kept at 0 °C. Stable for prolonged periods at rt.
Borane-dimethyl sulfide (BMS) parallels Borane-Tetrahydrofuran in hydroboration and reduction reactions. Its advantages are stability, solubility in various solvents, and higher concentration.
The hydroboration reaction tolerates many functional groups. A high level of acyclic diastereoselection is achieved in certain highly functionalized alkenes with BMS (eq 4)13a and also with borane-THF.13b,c Vinylic and allylic derivatives containing oxygen, sulfur, or nitrogen substituents react with high regioselectivity, placing boron at the b-position (Figure 2).6,14 Although such organoboranes are prone to elimination reactions, pure products can often be obtained by a careful control of the reaction conditions.
Reduction of Functional Groups:1,25,26 Carboxylic Acids and Derivatives.
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