335279-91-9Relevant academic research and scientific papers
Scope and limitations of the [1,2]-alkylsulfanyl (SMe, SEt and SCH2Ph) and sulfanyl (SH) migration in the stereospecific synthesis of substituted tetrahydrofurans
Eames, Jason,Kuhnert, Nikolai,Warren, Stuart
, p. 138 - 143 (2007/10/03)
Acid catalysed rearrangement of a series of 4-RS-1,3-diols (R = Me, Et, Bn and H) with toluene-p-sulfonic acid in dichloromethane gives stereospecifically substituted tetrahydrofurans via a [1,2]-SR shift in near quantitative yield. We comment on the structural variation of the migrating (RS) substituent and that of the migration origin and terminus on the outcome of the title reaction. We also report on the surprising similarity between an alkylsulfanyl (RS) and sulfanyl (SH) migrating group.
