- Preparation of fluorinated imides
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A direct method for the preparation of trifluoroacetimides has been extended to the preparation of trifluoroacetyl trifluoracetimide and the new compound trifluoromethylsulfuryl trifluoroacetimide. Points concerning previously reported syntheses of trifluoroacetyl isocyanate have also been clarified.
- Ye,Noftle
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p. 193 - 196
(2007/10/03)
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- TRIFLUOROACETIC ACID IN THE SYNTHESIS OF THIOCARBAMATES AND ESTERS OF THIOCARBOXYLIC ACIDS
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It was demonstrated by chromatographic mass spectrometry and NMR and IR spectroscopy that products of the reaction of trifluoroacetic acid with methyl thiocyanate - N-trifluoroacetyl S-methyl thiocarbamate, S-methyl trifluoroethanethioate, and N-trifluoroacetyltrifluoroacetamide - are formed simultaneously in the synthesis of thiocarbamates and esters of thiocarboxylic acids from aliphatic carboxylic acids and the nonisomerized thiocyanates in trifluoroacetic acid.
- Polivin, Yu. N.,Vinokurov, V. A.,Karakhanov, R. A.,Silin, M. A.,Ageev, E. A.,Tagavov, I. T.
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p. 1832 - 1834
(2007/10/02)
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- TRIFLUOROACETIC ACID IN THE SYNTHESIS OF THIOLCARBAMATES AND S-METHYL ALKANETHIOATES
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The major products of the reaction of 2-bromohexanoic acid with methyl thiocyanate in trifluoroacetic acid are S-methyl 2-bromohexanethioate (II) (55percent yield), S-methyl 2,2,2-trifluoroethanethioate (IV) (31percent yield), N-trifluoroacetyltrifluoroacetamide (V) (11percent yield), and N-trifluoroacetyl-S-methylthiolcarbamate (III) (29percent yield).N-2-Bromohexanoyl-S-methylthiolcarbamate (I), N-2-bromohexanoyltrifluoroacetamide (VI), 2-thiapropioamide (VII), and S-methyl hexanethioate (VIII) are also formed in minor amounts.
- Polivin, Yu. N.,Ageev, E. A.
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p. 178 - 180
(2007/10/02)
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- Reactions of Trifluoroacetyl Isocyanate
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Trifluoroacetyl isocyanate (1) can be obtained from trimethylsilyl isocyanate and trifluoroacetyl chloride. 1 reacts with trifluoroacetamide forming N,N'-bis(trifluoroacetyl)urea (2), which can also be obtained from trifluoroacetyl chloride and urea or N,N'-bis(trimethylsilyl)urea, respectively. 1 reacts with ammonia or various amines forming the trifluoroacetylsubstituted ureas 3 - 6, and hydrazine 7.From 1 and trifluoroacetic acid hexafluorodiacetamide (8) could be obtained. 1 reacts with tert-butylalcohol forming tert-butyl (trifluoroacetyl)carbamate (9).From 1 and N,N-dimethylformamide N,N-dimethyl-N'-(trifluoroacetyl)formamidine (10) could be obtained as well as N-(trifluoroacetyl)pyrrole-2-carboxamide (11) from pyrrole.
- Kiemstedt, Wolfgang,Sundermeyer, Wolfgang
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p. 919 - 925
(2007/10/02)
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- Trifluoroacetylation and Subsequent Pyrolysis of 2-Amino-2-oxazolines
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Treatment of 2-amino-5-phenyl-2-oxazoline (I) with trifluoroacetic anhydride gave 1,3-bis(2,2,2-trifluoroacetyl)-1-urea (II).Compound II was pyrolyzed at 120 deg C to give 2,2,2-trifluoroacetyl isocyanate (III) and 2,2,2-trifluoro-N-acetamide (IV).Compound II was readily hydrolyzed to give 1-(2,2,2-trifluoroacetyl)-3-urea (VI).Compound VI was pyrolyzed at 230 deg C to give 2,2,2-trifluoroacetamide (VII) and 2,2,2-trifluoro-N-(E)-styrylacetamide (VIII).It was considered that the formation of VIII proceeded through the intermediate 2-(2,2,2-trifluoroacetyloxy)-2-phenylethyl isocyanate (XI) or 1-(2,2,2-trifluoroacetyl)-3-(E)-styrylurea (XII), as shown in Chart 1.Keywords - 2-amino-2-oxazoline; trifluoroacetylation; pyrolysis; 1,3-bis(2,2,2-trifluoroacetyl)-1-alkylurea; O,N-bis(2,2,2-trifluoroacetyl)aminoethanol; 1-(2,2,2-trifluoroacetyl)-3-alkylurea; 1-(2,2,2-trifluoroacetyl)-3-alkenylurea
- Tanaka, Chiaki,Nasu, Keiko,Yamamoto, Noriko,Shibata, Megumi
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p. 3374 - 3376
(2007/10/02)
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