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Amer. Chem. Soc. 91, 7315 (1969). 9. W. Huckel and W. Kraus, Chem. Ber. 92, 1158 (1959). Hydroboration A remarkable variation of the hydride reduction is the addition to double bonds of diborane (B2H6) (7). Easily generated by the reaction of boron trifluoride etherate with sodium borohydride, the reagent may be used in the generating solution or may be distilled into a receiving flask containing an ether as solvent. Diborane reacts with unsaturated polar functional groups with results similar to those of the metal hydride reducing agents.

5 g (80%) of 4-methyl-l-pentanol, bp 151-153°/735 mm. D. eXo-NORBORNEOL FROM NORBORNENE: EXTERNAL GENERATION OF DlBORANE (3) B2H6 A 500-ml three-necked flask is fitted with a thermometer, a condenser, and a gas dispersion tube. A tube from the condenser outlet dips below the surface of mercury in a side-arm test tube. 1). 30 mole) of norbornene in 100 ml of THF is placed in the flask. The gas dispersion tube is immersed in the reaction liquid and connected with Tygon tubing to a 250-ml three-necked flask serving as the diborane generator.

Methoxyphenol (59% yield). III. Allylic and Benzylic Bromination with 7V-Bromosuccinimide As mentioned in an earlier section (cf. Chapter 1, Section III), allylic positions are subject to attack by free radicals resulting in the formation of stable allyl radicals. A^-Bromosuccinimide (NBS) in the presence of free-radical initiators liberates bromine radicals and initiates a chain reaction bromination sequence by the abstraction of allylic or benzylic hydrogens. Since NBS is also conveniently handled, and since it is unreactive toward a variety of other functional groups, it is usually the reagent of choice for allylic or benzylic brominations (7).

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Advanced Organic Synthesis, Methods and Techniques by Richard S. Monson

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