120749-52-2

Upstream product

• 120749-35-1 (2SR,3RS,4SR)-2,6-Dimethylphenyl 3-hydroxy-2-methyl-4-phenylsulfanylhexanoate 
• 35874-97-6 α-(phenylthio)butanal 
• 120749-36-2 (2RS,3RS,4RS)-2-Methyl-4-phenylsulfanylhexane-1,3-diol 
• 120749-36-2 (2RS,3RS,4SR)-2-Methyl-4-phenylsulfanylhexane-1,3-diol 
• 120749-36-2 (2SR,3RS,4SR)-2-Methyl-4-phenylsulfanylheptane-1,3-diol 

Relevant academic research and scientific papers

Stereochemical control in the synthesis of tetrahydrofurans by cyclisation of diols with [1,2]phenylsulfanyl migration

Acid catalysed rearrangement of a series of 4-PhS-1,3-diols with toluene-p-sulfonic acid in benzene gives stereospecifically substituted 3-PhS-tetrahydrofurans in excellent yield via a [1,2]-SPh shift. We comment on the structural variation at both the migration origin and terminus on the outcome of the title reaction and define its limits.

STEREOCHEMICAL CONTROL IN THE SYNTHESIS OF TETRAHYDROFURANS BY CYCLISATION OF DIOLS WITH PHENYLTHIO MIGRATION

Cyclisation of diols with PhS migration leads to tetrahydrofurans by inversion at both the migration origin and terminus.Cyclisation to a secondary migration terminus is controlled by stereochemical factors.