The first synthesis and X-ray structures of polyfluorinated 1,2-, 2,3- and 2,4a-dihydro-1,3-diazafluorenes Full article
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Journal of Fluorine Chemistry
ISSN: 0022-1139 |
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| Output data | Year: 2006, Volume: 127, Number: 7, Pages: 936-942 Pages count : DOI: 10.1016/j.jfluchem.2006.04.005 | ||
| Tags | fluorinated; en-amino-imine; indene; indeno[2,1-d]pyrimidine; dihydro-1,3-diazafluorene; ketone; condensation; X-ray structure | ||
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Abstract:
Acetic acid-catalyzed condensation of 2-amino-3-(1-imino-2,2,2-trifluoroethyl)-1,1,4,5,6,7-hexafluoroindene (1b) with acetone and cyclopentanone gives 5,6,7,8,9,9-hexafluoro-2,2-dimethyl-4-trifluoromethyl-2,3-dihydro-1,3-diazafluorene (2a) and 5,6,7,8,9,9-hexafluoro-4-trifluoromethyl-2,3-dihydro-1,3-diazafluorene-2-spiro-1'-cyclopentane (3a) together with small amounts of 5,6,7,8,9,9-hexafluoro-2,2-dimethyl-4-trifluoromethyl-1,2-dihydro-1,3-diazafluorene (2b) and 5,6,7,8,9,9-hexafluoro-4-trifluoromethyl-1,2-dihydro-1,3-diazafluorene-2-spiro-1'-cyclopentane (3b), respectively. When acted upon by (CH3)(2)SO4 compounds 2, 3 were converted into corresponding fluorine-containing 1-methyl-1,2dihydro-1,3-diazafluorenes 6, 7. 4a-Chloro-5,6,7,8,9,9-hexafluoro-2,2-dimethyl-4-trifluoromethyl-2,4a-dihydro-1,3-diazafluorene (8) has been synthesized by the interaction of compound 2 with SOCl2. Solution of compound 2 as well as 8 in CF3SO3H-CD2Cl2 generated 5,6,7,8,9,9-hexafluoro-2,2-dimethyl-4-trifluoromethyl-1,2,3,4-tetrahydro-1,3-diazafluorene-4-yl cation (2c). The structures of compounds 2,3, 6-8 have been determined by single crystal X-ray diffraction. (c) 2006 Elsevier B.V. All rights reserved.
Cite:
Karpov V.M.
, Platonov V.E.
, Rybalova T.V.
, Gatilov Y.V.
, Shakirov M.M.
The first synthesis and X-ray structures of polyfluorinated 1,2-, 2,3- and 2,4a-dihydro-1,3-diazafluorenes
Journal of Fluorine Chemistry. 2006. V.127. N7. P.936-942. DOI: 10.1016/j.jfluchem.2006.04.005 WOS Scopus РИНЦ OpenAlex
The first synthesis and X-ray structures of polyfluorinated 1,2-, 2,3- and 2,4a-dihydro-1,3-diazafluorenes
Journal of Fluorine Chemistry. 2006. V.127. N7. P.936-942. DOI: 10.1016/j.jfluchem.2006.04.005 WOS Scopus РИНЦ OpenAlex
Dates:
| Published print: | Jul 1, 2006 |
Identifiers:
| Web of science: | WOS:000238901300018 |
| Scopus: | 2-s2.0-33745215072 |
| Elibrary: | 13508100 |
| OpenAlex: | W2952700742 |