1593771-94-8

Basic information

• Product Name: C₁₂H₁₇⁽²⁾HO₂S
• CAS NO: 1593771-94-8
• Molecular Weight: 227.332
• Mol File: 1593771-94-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: C₁₂H₁₇⁽²⁾HO₂S(CAS DataBase Reference)
• NIST Chemistry Reference: C₁₂H₁₇⁽²⁾HO₂S(1593771-94-8)
• EPA Substance Registry System: C₁₂H₁₇⁽²⁾HO₂S(1593771-94-8)

Safety Data

• Hazardous Substances Data: 1593771-94-8(Hazardous Substances Data)

Upstream product

• 1593771-61-9 ((4-methylpentan-2-yl)sulfonyl)benzene 
• 52075-20-4 1-phenylsulphonyl-3-methyl butane 
• 3112-85-4 methylphenylsulfonate 

Relevant articles and documents

Lithium-titanium exchange of tertiary α-sulfonyl carbanions: Synthesis, structure, dynamics and reactivity of bis(1-sulfonylalkyl) titaniums

Lithium-titanium exchange of tertiary α-sulfonyl carbanions with ClTi(OiPr)3 and Cl2Ti(OiPr)2 in diethyl ether gave bis(1-sulfonylalkyl) titaniums and not the corresponding (1-sulfon-ylalkyl) titaniums. X-ray crystal structure analysis of di(iso-propoxy) bis[1-(phenylsulfonyl) cyclobutyl]titanium and di-(isopropoxy) bis[1-(phenylsulfonyl) isopropyl]titanium showed asymmetric distorted octahedral complexes, having hexaco-ordinate Ti atoms, two C-Ti bonds, four Ti-O bonds, and two four-membered Ti-O-S-Cα rings. According to 1H NMR spectroscopy bis(1-sulfonylcycloalkyl) titaniums are non-flux-ional at room temperature. This suggests that chiral bis(1-sulfonylalkyl) titaniums should be configurationally stable. The bis(1-sulfonylalkyl) titaniums are stable at room temperature towards β-H elimination. They selectively add to benzaldehyde in the presence of acetophenone but do not react with methyl iodide. The reaction of tertiary acyclic α-sulfonyl carbanions with ClTi(OiPr)3 in tetrahydrofuran (THF) gives different titanium derivatives with unspecified structures, which not only selectively react with benzaldehyde in the presence of acetophenone but are also alkylated by methyl iodide.

Divergent Reactivity of Alkyl Aryl Sulfones with Bases: Selective Functionalization of ortho-Aryl and α-Alkyl Units Enabled by a Unique Carbanion Transmetalation

The electron-accepting sulfonyl group exhibits a strong acidifying influence on neighboring α-H atoms. The Julia and related olefinations are based on this effect. Here a surprising reversal in the metalation selectivity of branched alkyl aryl sulfones is described. Such sulfones were found to initially undergo directed ortho-metalation with good regioselectivity, despite having a more acidic α-H atom. The structure of the alkyl unit profoundly, but predictably, influences the regioselectivity of the attack of the base. In β- and γ-branched ortho-(alkylsulfonyl)aryllithiums a transmetalation to the α-carbanion proceeds only upon warming. Correspondingly generated ortho- or α-carbanions were then selectively applied thus permitting access to synthetically interesting compound classes.