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Synthesis 1986; 1986(2): 125-128
DOI: 10.1055/s-1986-31493
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Herstellung und Isomerisierung von 1-Alken-3-yl-acetaten und 2-Alken-1-yl-acetaten

Antonio García Martínez* , Manuel Oliver Ruiz, José Luis Marco Contelles
  • *Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Complutense, 28040 Madrid, Spanien
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Publication Date:
20 August 2002 (online)

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Synthesis and Isomerization of 1-Alken-3-yl Acetates and 2-Alken-1-yl Acetates The allylic rearrangement of 1-alken-3-yl acetates in acetic acid containing sodium acetate proceeds at a slower rate but in higher yield than the rearrangement in the presence of strong proton acids. The predominant products are 2-alken-1-yl acetates. (E)-2-Hexen-1-yl acetate can be isomerized to the (Z)-isomer or rearranged to 1-hexen-3-yl acetate via the epoxide, depending upon the conditions of reduction of the epoxide.

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