ORGN 56 |
| The synthesis of secondary amines from primary amines and alkyl or benzyl halides is often complicated due to the nucleophilicity of the desired reaction product leading to undesired overalkylation. We now present a powerful approach to circumvent this problem via the rearrangement of iminophosphorane derivatives which can be derived from the reaction of benzyl azides with phosphites and phosphonites. This reaction delivers secondary phosphonamide derivatives in yields with up to 95 % which can be easily transferred into the corresponding amines by acidic hydrolysis. Different modes of activation of this rearrangement are compared and presented.
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New Reactions and Methodology
8:00 AM-12:00 PM, Sunday, August 19, 2007 BCEC -- 258B, Oral
Division of Organic Chemistry |
