Novel generation ponytails in fluorous chemistry: Syntheses of primary, secondary, and tertiary (nonafluoro-tert-butyloxy)ethyl amines
作者： Dénes Szabó , János Mohl , Ana-Maria Bálint , Andrea Bodor , József Rábai
DOI: 10.1016/J.JFLUCHEM.2006.06.020
关键词:
摘要: Abstract (Nonafluoro- tert -butyloxy)ethyl tosylate 4 was prepared in 65% yield from nonafluoro- -butanol 1 using commercially available reagents. Further reaction of with HNR R 2 (R = R = H, CH 3 ; = CH , (CH ) C 8 F 17 OC(CF affords the appropriate (CF COCH NR amines 20–69% yields. Improved overall yields [(CF ] 3− n to were obtained by CONa and (XCH (X = Cl, = 0, 1, 2, R = CH X = CH SO O, = 1, nitrogen mustards a similar reactive β-substituted ethyl amine. The title are mobile colorless liquids volatile steam. bulky fluorous ponytail CO(CH displays high acidic stability increases character almost as much classical straight-chain ponytail.
elsevier.com
sci-hub.se 参考文章(36)
Duncan Macquarrie, James H. Clark, Handbook of Green Chemistry and Technology ,(2002)
Michael Freemantle, ACS Award in Applied Polymer Science Chemical & Engineering News. ,vol. 83, pp. 39- 40 ,(2005)
J.F. Pilichowski, J.M. Lehn, J.P. Sauvage, J.C. Gramain, Synthese de coordinats macrocycliques polyazotes comportant une fonction amine secondaire discriminee Tetrahedron. ,vol. 41, pp. 1959- 1964 ,(1985) , 10.1016/S0040-4020(01)96560-3
Konstantinos Prevedouros, Ian T. Cousins, Robert C. Buck, Stephen H. Korzeniowski, Sources, fate and transport of perfluorocarboxylates. Environmental Science & Technology. ,vol. 40, pp. 32- 44 ,(2006) , 10.1021/ES0512475
Frank J. Pavlik, P. E. Toren, Perfluoro-tert-butyl alcohol and its esters Journal of Organic Chemistry. ,vol. 35, pp. 2054- 2056 ,(1970) , 10.1021/JO00831A089
T. J. Wallington, M. D. Hurley, J. Xia, D. J. Wuebbles, S. Sillman, A. Ito, J. E. Penner, D. A. Ellis, J. Martin, S. A. Mabury, O. J. Nielsen, M. P. Sulbaek Andersen, Formation of C7F15COOH (PFOA) and other perfluorocarboxylic acids during the atmospheric oxidation of 8:2 fluorotelomer alcohol. Environmental Science & Technology. ,vol. 40, pp. 924- 930 ,(2006) , 10.1021/ES051858X
István T. Horváth, Fluorous Biphase Chemistry Accounts of Chemical Research. ,vol. 31, pp. 641- 650 ,(1998) , 10.1021/AR970342I
Elwin de Wolf, Paul Ruelle, Joep van den Broeke, Berth-Jan Deelman, Gerard van Koten, Prediction of partition coefficients of fluorous and nonfluorous solutes in fluorous biphasic solvent systems by mobile order and disorder theory Journal of Physical Chemistry B. ,vol. 108, pp. 1458- 1466 ,(2004) , 10.1021/JP036751F
Floryan De Campo, Dominique Lastécouères, Jean-Marc Vincent, Jean-Baptiste Verlhac, Copper(I) Complexes Mediated Cyclization Reaction of Unsaturated Ester under Fluoro Biphasic Procedure The Journal of Organic Chemistry. ,vol. 64, pp. 4969- 4971 ,(1999) , 10.1021/JO990134Z
Grace J. Chen, Loomis S. Chen, Reactions of cesium perfluorotertiary alkoxides and perfluorotertiary alcohols with reactive halides Journal of Fluorine Chemistry. ,vol. 79, pp. 125- 131 ,(1996) , 10.1016/S0022-1139(96)03474-4