Ursula Biermann et.al.: Friedel-Crafts Alkylation of Alkenes: Ethylaluminum Sesquichloride Induced Alkylations with Alkyl Chloroformates

Author(s): Ursula Biermann, Juergen O. Metzger

Title: Friedel-Crafts Alkylation of Alkenes: Ethylaluminum Sesquichloride Induced Alkylations with Alkyl Chloroformates

Date of Upload: 1999

Article: Angew. Chem. Int. Ed. 1999, 38, No. 24, Department of Chemistry, University of Oldenburg, Carl-von-Ossietzky-Str. 9-11, 26129 Oldenburg, Germany

Keywords: Alkenes, Alkylations, Carbocations, Chloroformates, Fatty acids, sustainable development, renewable feedstock, vegetable oil, plant oil

Abstract:
The formal addition of propane to nonactivated double bonds can be achieved with isopropyl chloroformate (2) in the presence of Et3Al2Cl3. Thus, a 1:1 mixture of 10-isopropyloctadecanoic acid (3) and the 9-regioisomer is formed from oleic acid (1). The reaction may also be carried out with 1-alkenes by the addition of triethylsilane as a hydride donor.

URL: http://www.chemie.uni-oldenburg.de/oc/metzger/publikationen/pdf/83_engl.pdf (application/pdf)


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