VI. Protected Amines
- Page ID
- 24557
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The benzyloxycarbonyl protected amine 40 reacts with (diacetoxyiodo)benzene–iodine to give a product (41) that contains a new ring system (eq 16).55 The proposed mechanism for this reaction (Scheme 13) involves internal hydrogen-atom abstraction by a nitrogen-centered radical. Similar internal hydrogen-atom abstraction takes place when a nitrogen-centered radical is generated from a sulfonamidate.56 Such reactions are reminiscent of the hydrogen-atom abstraction by alkoxy radicals described in Chapter 6.
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