Fluoroolefin oxides. 1. A new method of synthesis of perfluorinated epoxyalkanes

Synthesis of 2,3-bis(perfluoroalkyl)quinoxalines and 2,3-bis(perfluoroalkyl)-1,4-benzoxazines from oxides of internal perfluoroolefins

“…In this work we have studied the interaction of internal octafluoro-2,3-epoxybutane (1) (trans:cis $ 90:10), dodecafluoro-3,4-epoxyhexane (2) (trans:cis $ 90:10) and dodecafluoro-2,3-epoxyhexane (3) (trans:cis $ 90:10) [9] with ophenylenediamine and 2-aminophenol for the purpose of the preparing of heterocyclic compounds containing two perfluoroalkyl substituents along with an aromatic fragment, 2,3-bis(perfluorialkyl)quinoxalines and 2,3-bis(perfluorialkyl)benzoxazines. To study the effect of a solvent polarity on the heterocyclization process the aprotic solvents possessing different polarity, dioxane and N,N-dimethylacetamide, have been used in the reactions.…”

“…4.2.2.2. Quinoxalinone(9) 19. F NMR [(CD 3 ) 2 SO]: d À115.9 (2F, q, 3 J FF = 1.4 Hz, CF 2 ), À80.7 (3F, t, 3 J FF = 1.4 Hz, CF 3 ).…”

“…Melting points were measured in open capillaries and are reported uncorrected. Oxiranes (1-3)[9] were prepared according to reported procedures.4.1. The reaction of oxirane 1 with o-phenylenediamine 4.1.1.…”

A route to fluorocontaining N,S-heterocycles via octafluoro-2,3-epoxybutane

“…Melting points were measured in open capillaries and are reported uncorrected. Oxirane (1) was prepared according to a reported procedure [17]. …”

“…Continuing our efforts directed towards synthesis of fluorocontaining heterocycles we report in the present paper on conversion of internal octafluoro-2,3-epoxybutane 1 (cis:trans $ 10:90) [17] into new N,S-heterocycles: bis(trifluoromethyl)dihydrobenzothiazine 2, bis(trifluoromethyl)bis(benzothiazine) 5 and trifluoromethylcontaining benzothiazolidine 6 using 2-aminothiophenol. To investigate the effect of a solvent on a direction of the reaction aprotic solvents possessing different polarity [18], such as toluene, dioxane, tetrahydrofuran, dimethoxyethane, acetonitrile, N,Ndimethylacetamide (DMAA) and dimethylsulfoxide (DMSO), have been tested.…”