On the reduction of tertiary radicals by samarium diiodide (SmI2)

T Nagashima, A Rivkin…

Index: Nagashima, Tadamichi; Rivkin, Alexey; Curran, Dennis P. Canadian Journal of Chemistry, 2000 , vol. 78, # 6 p. 791 - 799

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Citation Number: 4

Abstract

Reduction of o-iodophenyl 3-methylbut-2-enyl ether with samarium diiodide generates mixtures of 3-isopropyl-2, 3-dihydrobenzofuran and 3-(2-propenyl)-2, 3-dihydrobenzofuran along with a small amount of dimer. If a source of deuterium is present during the reduction, then the 3-isopropyl product predominates and this product is labeled with one deuterium. However, attempts to quench the putative tertiary organosamarium reagent by adding a ...