Synthesis and structure of reaction products obtained from 1,2-epoxyperfluorobutane and bifunctional nucleophilic reagents

Author： Filyakova T.   Kodess M.   Slepukhin P.   Zapevalov A.  

Publisher： MAIK Nauka/Interperiodica

ISSN： 1070-4280

Source： Russian Journal of Organic Chemistry, Vol.45, Iss.11, 2009-11, pp. : 1700-1706

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Abstract

1,2-Epoxyperfluorobutane readily reacts with bifunctional nucleophilic reagents to provide heterocyclic compounds with a pentafluoroethyl substituent. The reaction of this epoxide with thiourea and acetone thiosemicarbazone gave rise to 2-amino-5-pentafluoroethyl-5-fluoro-4(5H)-thiazolinone and 2-isopropylidenehydrazono-5-pentafluoroethyl-5-fluoro-4-thiazolidinone respectively. The reaction of 1,2-epoxyperfluorobutane with o-phenylenediamine and 2,3-diaminonaphthalene afforded in high yields 3-pentafluoroethyl-2(1H)-quinoxalinone and 3-(pentafluoroethyl)benzo[g]-2(1H)-quinoxalinone. The molecular and crystal structure of the obtained fluorine-containing heterocycles was established by XRD analysis.

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