Toward Novel Antioxidants: Preparation of Dihydrotellurophenes and Selenophenes by Alkyltelluride-Mediated Tandem SRN1/SHi Reactions1

…, J Malmström, CH Schiesser, LM Zugaro

Index: Engman, Lars; Laws, Melissa J.; Malmstroem, Jonas; Schiesser, Carl H.; Zugaro, Lisa M. Journal of Organic Chemistry, 1999 , vol. 64, # 18 p. 6764 - 6770

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Citation Number: 52

Abstract

Reaction of 1-(2-iodophenyl)-1-methyloxirane (12) with 2 equiv of sodium n-butyltellurolate (n-BuTeNa), generated by the sodium borohydride reduction of di-n-butyl ditelluride, in THF, affords 2, 3-dihydro-3-hydroxy-3-methylbenzo [b] tellurophene (13) in 62% yield, together with a small quantity of 1-(n-butyltelluro)-2-phenyl-2-propanol (27). This transformation presumably involves a tandem SRN1/SHi sequence. Similar reactions of 1-(benzylseleno) ...