Houben-Weyl Methods in Organic Chemistry: Diazonium Salts by Houben J., Weyl T.
By Houben J., Weyl T.
Methoden der Organischen Chemie (Methods of natural Chemistry, known as Houben-Weyl) is a customary reference paintings for chemists engaged in natural synthesis. In volumes on compound sessions, together with all Supplemental volumes, preparative tools are handled comprehensively and significantly. Tables of examples examine an important tools and exhibit their scope. targeted experimental methods are given for the easiest tools. The reactivity and extra reactions of every compound category also are provided. The huge use of formulation schemes help in making the German-language volumes extra effortlessly comprehensible to non-German readers.
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Extra resources for Houben-Weyl Methods in Organic Chemistry: Diazonium Salts (10/3)
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.
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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.