Carbon monoxide as a building block in organic synthesis: Part II. One-step synthesis of esters by alkoxycarbonylation of naturally occurring allylbenzenes,propenylbenzenes and monoterpenes |
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| Institution: | 1. Univ. Lille, CNRS, INRAE, Centrale Lille, UMR 8207 - UMET - Unité Matériaux et Transformations, F-59000 Lille, France;2. BASF Polyurethanes GmbH, Elastogranstraße 60, 49448 Lemförde, Germany;3. BASF SE, Carl-Bosch-Str. 58, 67056 Ludwigshafen am Rhein, Germany;1. Chemical Technology Division, CSIR-Institute of Himalayan Bioresource Technology, Palampur 176061, HP, India;2. Academy of Scientific & Innovative Research (AcSIR), Ghaziabad 201002, India;3. Department of Computational Sciences, Central University of Punjab, India, 15140 |
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| Abstract: | Various allylbenzenes (estragole, eugenol, eugenol methyl ether, safrole), propenylbenzenes (the iso compounds) and monoterpenes (limonene, isopulegol, isopulegyl acetate) were converted into the corresponding esters by alkoxycarbonylation at 4 MPa and 100 °C. Two palladium systems were used to catalyze this reaction: PdCl2(PPh3)2] and PdCl2(PPh3)2]/SnCl2·2H2O when larger amounts of linear ester are expected. This reaction was shown to be highly selective, since only the terminal carbon—carbon double bond was transformed. Isopulegol gave rise to a cyclocarbonylation reaction leading to the corresponding δ-lactone. |
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