S-Trifluoromethyl esters of thiocarboxylic acids, RC(O)SCF3

Tetrahedron Letters

Volumn 45, Issue 32, 2004, Pages 6101-6104

  Kremlev, Mikhail M ^a   Tyrra, Wieland ^b   Naumann, Dieter ^b   Yagupolskii, Yurii L ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Ukraine)

^b UNIVERSITY OF COLOGNE   (Germany)

Author keywords

Acid chlorides; Halide substitution; S Trifluoromethyl esters

Indexed keywords

AMMONIUM DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; CHLORIDE; ESTER DERIVATIVE; FLUORINE DERIVATIVE; HALIDE; METHYL GROUP; TETRAMETHYLAMMONIUM TRIFLUOROMETHYLTHIOLATE; THIOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 3142661629     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.06.073     Document Type: Article

References (20)

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5. Man E.H., Coffman D.D., Muetterties E.L. J. Am. Chem. Soc. 81:1959;3575-3577
6. Wessel W., Tyrra W., Naumann D.Z. Anorg. Allg. Chem. 627:2001;1264-1268
7. Tyrra, W.; Buslei, S.; Quadt, S. Unpublished results???
8. Bertrand F., Pevere V., Quiclet-Sire B., Zard S.Z. Org. Lett. 3:2001;1069-1071
9. Tyrra W., Naumann D., Hoge B., Yagupolskii Yu.L. J. Fluorine Chem. 119:2003;101-107
10. General procedure. To a solution of the corresponding acid chloride (2 mmol) in 5 mL acetonitrile at -30°C, a solution of tetramethylammonium trifluoromethanethiolate (2 mmol) in 10 mL acetonitrile was added drop-wise over a period of 10 min. The reaction mixture was warmed slowly to ambient temperature under stirring within 1 h, filtered from tetramethylammonium chloride and all volatile materials were evaporated at reduced pressure. The residue was extracted with diethyl ether and filtered again. Diethyl ether was evaporated and the crude material was purified by recrystallisation or distillation.
11. 3S: C, 38.25; H, 1.61; N, 5.57; S, 12.77. Found: C, 38.18; H, 1.62; N, 5.82; S, 12.16
12. 2S: C, 36.74; H, 1.54; S, 16.35. Found: C, 36.59; H, 1.32; S, 16.17
13. 2: C, 33.96; H, 1.42; S, 30.22. Found: C, 34.47; H, 1.22; S, 30.75
14. 3OS: C, 51.72; H, 3.03; S, 13.81. Found: C, 51.94; H, 2.92; S, 12.99
15. 3NOS: C, 35.82; H, 5.00; N, 6.96; S, 15.94. Found: C, 35.47; H, 4.78; N, 6.63; S, 15.61
16. 3OS: C, 53.71; H, 7.14; S, 11.95. Found: C, 53.31; H, 7.97; S, 10.76
17. FF≈1.6 Hz), -139.5 (m, F-2,6, 2F), -146.2 (tt, F-4, 1F), -160.3 (m, F-3,5, 2F)
18. 2: C, 32.24; H, 0.90; N, 4.18; S, 19.13. Found: C, 32.80; H, 0.78; N, 4.35; S, 18.87
19. FF=4.5 Hz), -127.5 (m, F-3,5, 2F), -133.6 (m, F-2,6, 2F)
20. 2S: C, 32.67; H, 0.34; S, 10.90. Found: C, 32.77; H, 0.15; S, 11.16