358725-37-8

Basic information

• Product Name: (+)-1,2,3,4,5-pentafluoro-6-{1-(S)-[1E-2-methylbuta-1,3-dienyloxy]ethyl}benzene
• CAS NO: 358725-37-8
• Molecular Weight: 278.222
• Mol File: 358725-37-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (+)-1,2,3,4,5-pentafluoro-6-{1-(S)-[1E-2-methylbuta-1,3-dienyloxy]ethyl}benzene(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-1,2,3,4,5-pentafluoro-6-{1-(S)-[1E-2-methylbuta-1,3-dienyloxy]ethyl}benzene(358725-37-8)
• EPA Substance Registry System: (+)-1,2,3,4,5-pentafluoro-6-{1-(S)-[1E-2-methylbuta-1,3-dienyloxy]ethyl}benzene(358725-37-8)

Safety Data

• Hazardous Substances Data: 358725-37-8(Hazardous Substances Data)

Upstream product

• 104371-20-2 (S)-1-(2',3',4',5',6'-perfluorophenyl)ethanol 
• 19493-09-5 Methylenetriphenylphosphorane 
• 473733-73-2 (-)-(E)-2-methyl-3-[(S)-1-(pentafluorophenyl)ethoxy]prop-2-enal 

Relevant articles and documents

Development of a new carbon - carbon bond forming reaction. New organic chemistry of sulfur dioxide. Asymmetric four-component synthesis of polyfunctional sulfones

At low temperature 1-alkoxy-1,3-dienes add to sulfur dioxide activated by a Lewis or Bronstedt acid and generate zwitterionic intermediates that can be quenched by enoxysilanes. The resulting β,γ-unsaturated silyl sulfinates can be desilylated and reacted with methyl iodide to provide polyfunctional sulfones. Exploratory studies of this four-component synthesis of sulfones are reported. Enantiomerically pure derivatives containing up to three new stereogenic centers can be obtained using enantiomerically pure (E,E)-1 -alkoxy-2-methylpenta-1,3-dienes derived from α-methyl benzyl alcohols, including the Greene's chiral auxiliary. The stereochemistry of the reactions is consistent with a mechanism involving the suprafacial hetero-Diels - Alder addition of sulfur dioxide to the 1-alkoxy-1,3-dienes that are rapidly ionized into zwitterionic intermediates.