Preparation of α-substituted S-phenylthio esters from 2-nitro-2-phenylthio oxiranes

Add time:07/12/2019    Source:sciencedirect.com

2-Nitro-2-phenylthio oxiranes (3), prepared by nucleophilic epoxidation of 1-nitro-1-phenylthio alkenes (1), react with a variety of heteroatomic nucleophiles to give α-substituted S-phenylthio esters (2). Of special note is the efficient reaction of 2-nitro-2-phenylthio oxiranes with boron trifluoride etherate in toluene at room temperature to give α-fluoro S-phenylthio esters (8).

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