Science of Synthesis

Matteson, D. S., Science of Synthesis, (2005) 6, 35.

Borane–dimethyl sulfide and borane–1,4-oxathiane are commonly used as hydroborating agents and are commercially available. Dimethyl sulfide is volatile and easily removed from reaction products by distillation, although its strong and obnoxious odor can be a problem. Borane–1,4-oxathiane utilizes a less odoriferous sulfide and is a useful alternative.[‌125‌] Oxathiane can be oxidized to the water-soluble sulfoxide with hypochlorite, without affecting the product trialkylborane.[‌126‌] A full report of the preparation and the utility of this reagent has appeared.[‌127‌]

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References

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• 8.Meeeee-Meee, (8888) 88/8e, 888.