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Communication | Regular issue | Vol 78, No. 6, 2009, pp.1433-1438
Published online, 25th February, 2009
DOI: 10.3987/COM-09-11643
Lossen-Type Rearrangement Products in the Reaction of N-(Phthalimidoyloxy)-3-phenylpropionate and -tosylate with Benzyl Alcohol

Shunsuke Takagi, Md. Chanmiya Sheikh, Asako Ogasawara, Masayuki Ohira, Hitoshi Abe, and Hiroyuki Morita*

*Department of Material Systems Engineering and Life Science, Faculty of Engineering, Toyama University, Gofuku 3190, Toyama 930-8555, Japan

Abstract

This paper reports the reaction of N-(phthalimidoyloxy)-3-phenylpropionate (2a) and -tosylate (6) with benzyl alcohol as a nucleophile to afford the products via Lossen-type rearrangement. To study the scope of this reaction mechanism, we also studied the reaction of several N-sulfonyloxyimide derivatives with benzyl alcohol under similar conditions and found that the same types of products were obtained in high yields.