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Odorless Reagent for the Introduction of S-tert-Butyl Group

2-(tert-Butyl)isothiouronium Bromide (1) is an odorless solid utilized as a reagent to introduce the tert-butylthio group. For instance, introduction of the tert-butylthio group proceeds by treating 1 with arylhlides in high yields in the presence of palladium catalyst.1) In addition, the tert-butyl group can be removed by treating with Brønsted acid or Lewis acid and a thioketal like 2 is afforded in the presence of acetone. On the other hand, by adding a catalytic amount of base, 1 can introduce the tert-butylthio group to ethyl bromoacetate.2)

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Potassium tert-Butoxide (= KOtBu)
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Sodium Ethoxide (= EtONa)

References

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