Sulfur Reagents in Organic Synthesis by Patrick Metzner, Andre Thuillier, A. R. Katritzky

By Patrick Metzner, Andre Thuillier, A. R. Katritzky

Designed for the training natural chemist, this e-book info over 100 experimental tactics utilizing sulfer compounds in natural synthesis. lots of those equipment are new to the literature, having been released due to the fact that 1991, and illustrate the awesome versatility of using sulfur reagents. Examples are easy to accomplish and intensely valuable, and as such this publication can be a useful reduction to all interested in artificial natural chemistry, no matter if in educational or business laboratories.

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4. Pyridinium Dichromate (PDC) It is important to stress the fact that no fragmentation needs to occur wherever a stable carbocation can be formed. 184 O O O N OH O O O O N PDC SO2Me O SO2Me O O O 76% Ref. 184a No fragmentation occurs regardless of the very stabilized carbocations that it would produce. Sometimes, treatment of primary alcohols with PDC leads to the formation of dimeric esters186 arising from the oxidation of acyclic hemiacetals, formed by reaction of the starting alcohol with an intermediate aldehyde.

Tetrahedron Lett. 1987, 28, 239. ; Tetrahedron Lett. 1987, 28, 671. ; Rabanal, R. Chem. 1987, 65, 339. e) Pirrung, M. ; Thomson, S. Chem. 1988, 53, 227. ; Q. ; Sulikowski, G. ; Tetrahedron 2002, 58, 4403. ; Zannetti, M. Chem. 1995, 60, 7870. 37 a) White, J. ; Jayasinghe, L. ; Tetrahedron Lett. 1988, 29, 2139. ; Tetrahedron Lett. 1987, 28, 3091. 38 a) Smith, A. ; Pitsinos, E. ; Scarlato, G. ; Nicolaou, K. Soc. 1993, 115, 7612. Bull. 1987, 35, 996. Bull. 1986, 34, 4629. 39 a) Danishefsky, S. ; Selnick, H.

A) Ref. 46b. b) Anderson, R. Chem. 1985, 50, 4781. ; Tetrahedron Lett. 1985, 26, 2693. ; Tetrahedron Lett. 1989, 30, 103. Evans, D. ; Bender, S. ; Tetrahedron Lett. 1986, 27, 799. , R. ; Tagat, J. ; Johnston, B. ; Heterocycles 1987, 25, 33. a) Ref. 97. b) Shing, T. K. Chem. 2000, 65, 7059. c) Holum, J. Chem. 1961, 26, 4814. Chem. 1977, 42, 813. Walba, D. ; Stoudt, G. ; Tetrahedron Lett. 1982, 23, 727. ; Robins, M. ; Tetrahedron 1984, 40, 125. 4. 4. Pyridinium Dichromate (PDC) O PyH O O Cr O Cr O O PyH O The slow addition of one equivalent of pyridine on a concentrated aqueous solution of CrO3 leads to the formation of pyridinium dichromate (PDC), which can be precipitated by the addition of 4 volumes of acetone per volume of water and cooling at À208C.

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