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Monatshefte für Chemie / Chemical Monthly

, Volume 127, Issue 2, pp 177–183 | Cite as

Regioselective amidation of allylic α-hydroxyphosphonates with Nitriles: A convenient route to (3-acetylamino-1-alkenyl)-phosphonates

  • E. Öhler
  • S. Kanzler
Organische Chemie Und Biochemie

Summary

Reaction of dialkyl (1-hydroxy-2-alkenyl)- and (1-hydroxy-2-cycloalkenyl)phosphonates (1) with acetonitrile in the presence of trifluoromethane sulfonic acid (TfOH) affords regiospecifically and with high (E)-stereoselectivity the 1,3-transposed acetamides3 in modest to good yields.

Keywords

Dialkyl (1-hydroxy-2-alkenyl)phosphonates Dialkyl (3-acetylamino-1-alkenyl)phosphonates 1,3-Transposition Ritter reaction 

Regioselektive Amidierung von allylischen α-Hydroxyphosphonaten mit Nitrilen: Ein einfacher Weg zu (3-Acetylamino-1-alkenyl)phosphonaten

Zusammenfassung

(1-Hydroxy-2-alkenyl)- und (1-Hydroxy-2-cycloalkenyl)phosphonate (1) reagieren mit Acetonitril in Gegenwart von Trifluormethansulfonsäure (TfOH) in mäßigen bis guten Ausbeuten regiospezifisch und mit hoher (E)-Stereoselektivität zu den 1,3-umgelagerten Acetamiden3.

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References

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Copyright information

© Springer-Verlag 1996

Authors and Affiliations

  • E. Öhler
    • 1
  • S. Kanzler
    • 1
  1. 1.Institut für Organische Chemie der Universität WienWienAustria

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