Reductive opening of phenyl substituted thiacycloalkanes: New way for sulphur-containing organolithium compounds

J Almena, F Foubelo, M Yus

Index: Almena, Juan; Foubelo, Francisco; Yus, Miguel Tetrahedron, 1997 , vol. 53, # 15 p. 5563 - 5572

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Citation Number: 32

Abstract

The reaction of 2-phenyl substituted four, five and six membered thiacycloalkanes (1, 4 and 7) with lithium and a catalytic amount of DTBB (5 mol%) in THF at− 78° C leads to the corresponding sulphur-containing benzylic organolithium compounds (2, 5 and 8), which by reaction with different electrophiles [D2O, Me3SiCl, ButCHO, Me2CO, Et2CO,(CH2) 4CO, CO2] followed by hydrolysis with water afford the expected functionalised mercaptans (3, ...