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Mechanism for Compound 11 to Compound 22

Similar to the tale of brave Pocahontas saying goodbye to John Smith, here we have the tale of compound 11 separating itself from two its lovers: the virtuous sulfoxide leaving group and the beloved hydroxide group at the heart of the molecule. Both are to be replaced by a boring and commonplace hydrogen. Although three steps are needed for this division to occur, the second step is known as the Barton-McCombie deoxygenation reaction and is essential to understanding the why behind the separation of once wonderful partners in chemical stability.