Standard Article

Isopropyldiphenylsulfonium Tetrafluoroborate

  1. Tony Durst1,
  2. Robert N. Ben1,
  3. Marie-Noelle Roy2

Published Online: 16 SEP 2013

DOI: 10.1002/047084289X.ri081m.pub2

e-EROS Encyclopedia of Reagents for Organic Synthesis

e-EROS Encyclopedia of Reagents for Organic Synthesis

How to Cite

Durst, T., Ben, R. N. and Roy, M.-N. 2013. Isopropyldiphenylsulfonium Tetrafluoroborate. e-EROS Encyclopedia of Reagents for Organic Synthesis. .

Author Information

  1. 1

    University of Ottawa, Ottawa, Ontario, Canada

  2. 2

    Université de Montréal, Montréal, QC, Canada

Publication History

  1. Published Online: 16 SEP 2013

Chemistry Terms

Choose one or more boxes to highlight terms.

Abstract

original image

[1660-43-7] C15H17BF4S (MW 316.20)

(transformation of carbonyls to gem-dimethyloxiranes;2 conversion of α,β-unsaturated systems3 and diene esters4 to geminal substituted cyclopropanes)

Preparative Methods: this reagent is not commercially available and must be made prior to use. The ylide isopropylidenediphenylsulfurane, obtained by deprotonation with an appropriate base, is usually formed in situ and used immediately because of its extremely low stability.2 Two methods have been reported for the preparation of the sulfurane. Ethyldiphenylsulfonium tetrafluoroborate (formed by the reaction of diphenyl sulfide with triethyloxonium tetrafluoroborate, eq 1) is suspended in a solution of DME. The ylide is formed by addition of LiCHCl2 at −70 °C and reacted with MeI (1.1 equiv). The desired sulfonium salt precipitates from solution. The isopropylidenediphenylsulfurane is formed by addition of LDA to this suspension at −78 °C (eq 2).2

original image(1)
original image(2)

A second, but less efficient, method of preparation involves the reaction of diphenyl sulfide, AgBF4, and neat isopropyl iodide (eq 3).2

original image(3)

Three different base/solvent systems have been used to generate the isopropylidenediphenylsulfurane ylide: DME/LiCHCl2, t-BuOK/THF,5 and PhLi/THF.6 All methods have proven equally efficient. Different diastereomer ratios have been obtained with the t-BuOK/THF method compared to the other systems.7

Featured Compounds

VIEW

  1. 1 - 47
Compound Information
Molecular Weight:316.165
Molecular Formula:C15H17BF4S
InChIKey:OYVGOJMOYZVZFZ-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:186.273
Molecular Formula:C12H10S
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:189.987
Molecular Formula:C6H15BF4O
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:302.139
Molecular Formula:C14H15BF4S
InChIKey:OMJIKEGJWFKACN-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:21.976
Molecular Formula:CH3Li
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:90.866
Molecular Formula:CHCl2Li
InChIKey:XJBGQVPLRFIVLG-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:90.121
Molecular Formula:C4H10O2
InChIKey:XTHFKEDIFFGKHM-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:169.9922
Molecular Formula:C3H7I
InChIKey:FMKOJHQHASLBPH-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:194.673
Molecular Formula:AgBF4
InChIKey:CCAVYRRHZLAMDJ-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:106.1219
Molecular Formula:C7H6O
InChIKey:HUMNYLRZRPPJDN-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:228.353
Molecular Formula:C15H16S
InChIKey:KQUICRUYRJSYKC-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:148.2017
Molecular Formula:C10H12O
InChIKey:GIMKHGWDFQQNSB-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:372.6192
Molecular Formula:C26H42O
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:414.6989
Molecular Formula:C29H48O
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:96.1271
Molecular Formula:C6H8O
InChIKey:FWFSEYBSWVRWGL-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:138.2069
Molecular Formula:C9H14O
InChIKey:IXFKDMXWPMQKQD-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:195.2582
Molecular Formula:C11H17NO2
InChIKey:NPDJEMQVVUQPQO-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:237.3379
Molecular Formula:C14H23NO2
InChIKey:BSYMBESYVSNTRX-USQDWFKJSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:297.972
Molecular Formula:C8H10Br2O2
InChIKey:MDIQXIJPQWLFSD-INEUFUBQSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:270.2784
Molecular Formula:C13H18O6
InChIKey:CMZOUPWUYOCRDR-SFECMWDFSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:354.4379
Molecular Formula:C19H30O6
InChIKey:PLOCHUCDFQIBQI-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:156.1791
Molecular Formula:C8H12O3
InChIKey:KVSRWNPBUMDYOQ-WDSKDSINSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:520.7303
Molecular Formula:C28H44O7Si
InChIKey:DEBHZYXHSMQNSZ-MDTNNAMMSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:562.81
Molecular Formula:C31H50O7Si
InChIKey:FPZBRGMTBKOYQK-DTPIWGLOSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:152.1904
Molecular Formula:C9H12O2
InChIKey:CWXMXSNBCWFLOY-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:194.2701
Molecular Formula:C12H18O2
InChIKey:IKAAFZORZAMSBU-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:194.2701
Molecular Formula:C12H18O2
InChIKey:YTUSGSYRKKRTMA-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:72.1057
Molecular Formula:C4H8O
InChIKey:WYURNTSHIVDZCO-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:120.1485
Molecular Formula:C8H8O
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:162.2283
Molecular Formula:C11H14O
InChIKey:MUKMIRQCNGESTE-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:107.123
Molecular Formula:C6H14LiN
InChIKey:ZCSHNCUQKCANBX-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:84.933
Molecular Formula:CH2Cl2
InChIKey:YMWUJEATGCHHMB-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:162.2283
Molecular Formula:C11H14O
InChIKey:VHAZKKKEUDNFJE-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:511.98
Molecular Formula:C18BF15
InChIKey:OBAJXDYVZBHCGT-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:246.4201
Molecular Formula:C15H22OSi
InChIKey:DJNPNSHAPQKOQL-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:288.4998
Molecular Formula:C18H28OSi
InChIKey:OPMWGQDQBNXBNS-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:64.055
Molecular Formula:C4H9Li
InChIKey:BKDLGMUIXWPYGD-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:154.2493
Molecular Formula:C10H18O
InChIKey:DKZZGPKCUOZNMW-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:141.928
Molecular Formula:C4H10BF3O
InChIKey:KZMGYPLQYOPHEL-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:156.1791
Molecular Formula:C8H12O3
InChIKey:MODQTBIIPUTENE-SNAWJCMRSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:198.2588
Molecular Formula:C11H18O3
InChIKey:VLKGMBWEIUZZQB-WPZUCAASSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:196.673
Molecular Formula:C11H13ClO
InChIKey:YRLUYGOKNFHTBC-CBAPKCEASA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:238.753
Molecular Formula:C14H19ClO
InChIKey:FNFGMRFTGMOBPV-PEFMBERDSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:183.3746
Molecular Formula:C6H18NNaSi2
InChIKey:WRIKHQLVHPKCJU-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:492.163
Molecular Formula:C3F9O9S3Sc
InChIKey:HZXJVDYQRYYYOR-UHFFFAOYSA-K
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:309.236
Molecular Formula:C11H15CrNO6
InChIKey:XXLBAPDYJMKDNK-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:278.1789
Molecular Formula:C10H10CrO6
InChIKey:UFGISCJPTCJYNH-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound

VIEW

  1. 1 - 47