vinylthiylation of octafluorotoluene and its derivatives
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Phosphorus, Sulfur, and Siliconand the Related ElementsPublication details, including instructions forauthors and subscription information:http://www.tandfonline.com/loi/gpss20
Vinylthiylation ofOctafluorotoluene and itsDerivativesSvetlana V. Amosova a a & Galina M. Gavrilova aa A. E. Favorsky Irkutsk Institute of Chemistry ,Irkutsk, RussiaPublished online: 16 Aug 2006.
To cite this article: Svetlana V. Amosova & Galina M. Gavrilova (2005) Vinylthiylationof Octafluorotoluene and its Derivatives, Phosphorus, Sulfur, and Silicon and theRelated Elements, 180:5-6, 1435-1436, DOI: 10.1080/10426500590912925
To link to this article: http://dx.doi.org/10.1080/10426500590912925
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Phosphorus, Sulfur, and Silicon, 180:1435–1436, 2005Copyright © Taylor & Francis Inc.ISSN: 1042-6507 print / 1563-5325 onlineDOI: 10.1080/10426500590912925
Vinylthiylation of Octafluorotoluene and its Derivatives
Svetlana V. AmosovaGalina M. GavrilovaA. E. Favorsky Irkutsk Institute of Chemistry, Irkutsk, Russia
1,2,5-Tri(vinylthio)-4-trifluoromethyl-3,6-difluorobenzene (1) and 1-dimethylamino-2,5-di(vinylthio)-4-trifluoromethyl-3,6-difluorobenzene(2) were obtained in 13 and 73% yields, respectively, by the reactionof octafluorotoluene with a three-fold excess of the ethenethiolateanion (which can readily be generated from divinylsulfide under theaction of sodium in liquid ammonia) at 10–20◦C in DMF (which is usedinstead of liquid ammonia). The compound 2 is formed as a result oftransamidation with dimethylformamide (Scheme).
The interaction of 1-amino-4-trifluoromethyl-2,3,5,6-tetrafluoroben-zene (3) with the ethenethiolate anion in DMF at 10–20◦C affords1-amino-2,5-di(vinylthio)-4-trifluoromethyl-3,6-difluorobenzene (4) in18% yield (Scheme).
SCHEME
Received July 9, 2004; accepted October 5, 2004.This work was supported by the RFBR (Grant No. 02-03-32844).Address correspondence to Svetlana V. Amosova, A. E. Favorsky Irkutsk Institute
of Chemistry SB RAS, 1 Favorsky Str., Irkutsk 664033, Russia. E-mail: [email protected]
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1436 S. V. Amosova and G. M. Gavrilova
Therefore we have shown that when perfluorobenzenes contain anelectron-withdrawing substituent (CF3), solvents (NH3, DMF) also actas reactants, posing strong competition to the ethenethiolate anion innucleophilic substitution reactions. These results allow the targetedsynthesis of polyfunctional perfluorobenzenes.
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