An extremely mild 3-aza-claisen reaction. 2. New conditions and the rearrangement of α-heteroatom substituted amides

Walters, Michael A.; Hoem, A. B.; Arcand, Helene R.; Hegeman, Adrian D.; Mcdonough, C. S.

doi:10.1016/s0040-4039(00)60316-7

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Cited by 29 publications

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“…70 N-Allylamides can be converted to pentenylnitriles under extremely mild aza-Ciaisen conditions 42 • 43 at room temperature and essentially neutral condition in moderate to good yields. When aliylamide 43 71 was treated with a variety of dehydrating agents like 2Ph 3 P, 2CCI 4 , 3Et 3 N or Br 2 .PPh 3 , 2Et 3 N or 31 2 .P(OEt) 3 , 3Et 3 N in dichloromethane, pentenylnitrile 73 was obtained through initial formation of ketenimine 72. 3.…”

Section: ~ ~+M~~ Me~~mentioning

confidence: 99%

Aza‐Claisen Rearrangement

2010

Comprehensive Organic Name Reactions and Reagents

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This brief review presents an overview on aza-Ciaisen rearrangement with an emphasis on recent developments, e.g. ketene-aza-Ciaisen rearrangement, aza-Ciaisen rearrangement by acid-catalyzed Michael addition and palladium complex-catalyzed aza-Ciaisen rearrangement etc. Contents 1. Introduction 2. Thermal aza-Ciaisen rearrangement 3. Ketene-aza-Ciaisen rearrangement 4. Catalyzed aza-Ciaisen rearrangement 4.1. Bronstead and Lewis acid catalyzed rearrangement 4.2. Aza-Ciaisen rearrangement initiated by acid-catalyzed Michael addition 4.3. Aza-Claisen rearrangement catalyzed by Pd-complexes 5. Conclusion

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Section: ~ ~+M~~ Me~~mentioning

confidence: 99%