Abstract
The Claisen rearrangement is a [3,3]-sigmatropic rearrangement which is an important method for new C-C bond formation in organic synthesis. This reaction is a typical thermal reaction that requires a high temperature and long reaction time. In this paper, the acceleration effects of the iron (III) chloride (FeCl3) catalyst and microwave irradiation during the Claisen rearrangement reaction of allyloxyarene derivatives are reported. The FeCl3 catalyst was able to initiate the reaction at low temperature and induced the subsequent cyclization reaction. The moderation of excellent yields was obtained in a short reaction time. The formation of complex ferric-arenes under microwave irradiation conditions to efficiently absorb the microwaves was expected and confirmed.
Highlights
Several environmental problems such as global warming and pollution caused by an industrial process become the world concern
The Claisen rearrangement is a [3,3]-sigmatropic rearrangement which is an important method for new C-C bond formation in organic synthesis
The ratio of the products was identified by High Performance Liquid Chromatography (HPLC) analysis using a Shimadzu LC-20A system equipped with a UV detector
Summary
Several environmental problems such as global warming and pollution caused by an industrial process become the world concern. Since discovered in 1912, the Claisen rearrangement reaction has been developed into one of the most powerful C-C bond forming methods in organic synthesis [1]. This reaction normally takes place by heating the O-allyl ether of phenols or enols, forming the C-allyl compound. Microwave irradiation has been demonstrated to be a powerful tool for organic synthesis since it offers significant advantages over conventional heating, e.g., cleaner method, quick reaction, high chemical yield, and high selectivity. The microwave heating effects on the Claisen rearrangement reaction of allyloxyarene derivatives in the presence of the FeCl3 catalyst were investigated
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