Reaction of singlet oxygen with thioanisole in ionic liquid-acetonitrile binary mixtures

Organic Letters

Volumn 12, Issue 22, 2010, Pages 5116-5119

  Baciocchi, Enrico ^a   Chiappe, Cinzia ^b   Fasciani, Chiara ^a   Lanzalunga, Osvaldo ^a   Lapi, Andrea ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

^b UNIVERSITY OF PISA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 78449276969     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol102263w     Document Type: Article

References (26)

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13. 2N] (85 mPa s) (6b) the sulfoxide yield remains constant from 1 M to neat liquid.
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17. 2N] that it makes it the least efficient IL for sulfoxidation of thioanisole as neat solvent, also less efficient than the pyrrolidinium IL (vide infra).
18. Tokuda, H.; Hayamizu, K.; Ishii, K.; Susan, M. A. B. H.; Watanabe, M. J. Phys. Chem. B 2005, 109, 6103
19. For a microreview, see: Ueno, K.; Tokuda, H.; Watanabe, M. Phys. Chem. Chem. Phys. 2010, 12, 1649
20. nmim]Br in different molecular solvents showed that, at low concentrations, the ionic association constant decreases with increasing alkyl chain length.
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23. s[PhSMe]) ratio (ca. 0.9) does not significantly change on passing from neat MeCN to neat ILs.
24. 2N] is clearly outside it. For details, see Table S2 in SI.
25. -1 linear plot is expected with an intercept value of 1/2 fK ′ where f is the fraction of 3 undergoing product formation. Since for MeOH and imidazolium ILs f = 1, the highest intercept value is reached.
26. 2N] (0.617), it would appear that, for the persulfoxide 2 stabilization, the electrostatic interactions are more important than the capability of hydrogen bond formation: Crowhurst, L.; Mawdsley, P. R.; Perez-Arlandis, J. M.; Salter, P. A.; Welton, T. Phys. Chem. Chem. Phys. 2003, 5, 2790