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Synthesis 1995; 1995(2): 159-161
DOI: 10.1055/s-1995-3885
short paper
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Facile Aluminum(III) Chloride Catalyzed Preparation of β,γ-Unsaturated O-Aryl Esters from Allylsilanes and Aryl Chloroformates

George A. Olah* , David S. VanVliet, Qi Wang, G. K. Surya Prakash1
  • *Donald P. and Katherine B. Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, Los Angeles, California 90089-1661, USA
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Publication Date:
31 December 2000 (online)

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The aluminum trichloride catalyzed reaction of phenyl chloroformate (1a) with allylsilanes 2a-e gives phenyl 3-alkenoates in excellent yields. The reaction with allyltrimethylsilane 2a also works with a number of para substituted aryl chloroformates 1b-f.

aluminum chloride - allylsilanes - aryl chloroformates - O-aryl esters - SE2’ mechanism