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S- vs. O-alkylation using sodium sulfinates

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rolnor:
Yields in patents can be lower than 1% in some cases.

Babcock_Hall:
When diisopropyl bromomethylphosphonate comes in, I will test it using sodium phenylsulfinate, because I have the product that I can use as a standard.  At some point, I will also test the corresponding diethyl toluenesulfonate.  I did this once before, and I had some product formation, but not quite as much as I had hoped for.

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