Preparation. We have already covered these methods nucleophilic ring opening of epoxides by ammonia and amines. addition of nitrogen nucleophiles to aldehydes and ketones to form imines reduction of imines to amines reduction of amides to amines by LiAlH 4 reduction of nitriles to a 1° amine
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Alkyl Halide Alkyl amine
Note retention of configuration, trans trans
Step 1: Reaction of a 1° amine with the nitrosyl cation.
Step 2: Protonation followed by loss of water.
1. Lose a proton to give an alkene.
2. React with a nucleophile to give a substitution product.
3. Rearrange and then react by Steps 1 and/or 2.
Similar to pinacol rearrangement
Elimination of water to yield tertiary carbocation.
This is a protonated ketone!
1,2 rearrangement to yield resonance stabilized cation.
Problem:What reagents and experimental conditions will bring about this conversion?
Step 1: Oxidation of a 3° amine gives an amine oxide.
Step 2: If the amine oxide has at least one -hydrogen, it undergoes thermal decomposition to give an alkene.