Thiocarbonyl Compounds as Specific Tools for Organic Synthesis
作者： Patrick Metzner
关键词:
摘要: Thiocarbonyl compounds (thioamides, thioesters, thioketones...) react readily with a large variety of reagents (nucleophiles, electrophiles and radicals) due to their weak C=S bond the aptitude sulfur stabilise an adjacent charge or radical centre. Thus, nucleophilic additions, deprotonation, sigmatropic rearrangements are often more facile than in oxygen series. Moreover, number specific reactions have been uncovered: thiophilic addition nucleophiles, Michael enethiolates, Eschenmoser reaction, oxidation sulfines, [4+2] [3+2] cycloaddition 1,3-dienes 1,3-dipoles. Far from being purely exotic species, thiocarbonyl now efficient tools indeed used multi-step synthetic schemes leading various products biological interest.
springer.com
springerlink.com参考文章(243)
Jürgen Voss, Synthesis of Thioesters and Thiolactones Reference Module in Chemistry, Molecular Sciences and Chemical Engineering#R##N#Comprehensive Organic Synthesis. ,vol. 2, pp. 435- 460 ,(1991) , 10.1016/B978-0-08-052349-1.00164-5
Kazumi Shiosaki, 3.7 – The Eschenmoser Coupling Reaction Reference Module in Chemistry, Molecular Sciences and Chemical Engineering#R##N#Comprehensive Organic Synthesis. ,vol. 3, pp. 865- 892 ,(1991) , 10.1016/B978-0-08-052349-1.00051-2
David Crich, William B. Motherwell, Free Radical Chain Reactions in Organic Synthesis ,(1992)
Patrick Metzner, André Thuillier, Sulfur reagents in organic synthesis Academic Press. ,(1994)
Renji Okazaki, Chapter 5 Chemistry of thioaldehydes Organosulfur Chemistry. ,vol. 1, pp. 225- 258 ,(1995) , 10.1016/S1099-8268(07)80016-3
Ernst Schaumann, Synthesis of Thioamides and Thiolactams Reference Module in Chemistry, Molecular Sciences and Chemical Engineering#R##N#Comprehensive Organic Synthesis. ,vol. 2, pp. 419- 434 ,(1991) , 10.1016/B978-0-08-052349-1.00163-3
Andreas Brutsche, Klaus Hartke, Dithio- und Thionester, 55. Synthese vonN-geschützten, optisch aktiven α-Aminothionsäureestern Liebigs Annalen der Chemie. ,vol. 1992, pp. 921- 925 ,(1992) , 10.1002/JLAC.1992199201152
Antonella Capperucci, Alessandro Degl'Innocenti, M.Cristiana Ferrara, Bianca F. Bonini, Germana Mazzanti, Paolo Zani, Alfredo Ricci, Thiophilic allylation of dithioesters and trithiocarbonates Tetrahedron Letters. ,vol. 35, pp. 161- 164 ,(1994) , 10.1016/0040-4039(94)88190-1
Gordon W. Kirby, Alistair W. Lochead, Sharon Williamson, Dienophilic thioaldehydes and dithioesters formed by base-catalysed cleavage of alkyl phthalimidosulfanylacetates Journal of The Chemical Society-perkin Transactions 1. pp. 977- 984 ,(1996) , 10.1039/P19960000977
Nadia Pelloux-Léon, Roger Arnaud, Jean-Louis Ripoll, Pierre Beslin, Yannick Vallée, Thioacrolein S-oxide Tetrahedron Letters. ,vol. 38, pp. 1385- 1388 ,(1997) , 10.1016/S0040-4039(97)00026-9