Vogel reaction

Ammonium thiocyanate test (Vogel reaction) adding a few crystals of ammonium thiocyanate to a neutral or acid solution of cobalt(II) a blue colour appears owing to the formation of tetrathiocyanatocobaltate(II) ions ... 

Fester [18] has made this modification to his recipe by promoting the idea that bubbling HCI gas into the safrole/48% aq HBr reaction mix one can affect dehydration allowing dominant bromination to occur. Strike does not know if that actually works. Could be. But what Strike and Eleusis draw on are the examples given by Vogel [37 p277]. 

References Journal of Chemical Education, v14, pg542 Organic Reactions volume 3 Vogels Elementary Practical Organic Chemistry, pg574... 

The atom economy for this process is 86.5% (100 X 116/134), which is reasonable. To calculate the E-factor and EMY further information is needed. From published literature (Vogel s Practical Organic Chemistry ), a standard procedure is to mix butanol (37 g) with glacial acetic acid (60 g), and a small amount of sulfuric acid catalyst (ignored in all calculations). Following completion of the reaction the mixture is added to water (250 g). The crude ester is washed further with water (100 g), then saturated sodium bicarbonate solution (25 g) and finally water (25 g). After drying over 5 g of anhydrous sodium sulfate the crude ester is distilled to give product (40 g) in a yield of 69%. 

Yang H, Vogel W, Lamy C, Alonso-Vante N. 2004. Structure and electrocatalytic activity of carbon-supported Pt-Ni alloy nanoparticles toward the oxygen reduction reaction. J Phys ChemB 108 11024-11034. 

In 1974, Vogel and his coworkers62) reported the first synthesis of the syn-benzene bisepisulfide 119 and its thermal behavior. The bisepisulfide 119 is thermola-bile and decomposes at 20 °C with a half-life of about 30 min to form benzene and sulfur as final products. When the reaction was carried out in the presence of 4-phenyl-1,2,4-triazoline-3,5-dione (PTD), 119 gave the product 120 which corres-... 

An interesting pericyclic-anionic-pericyclic domino reaction showing a high stereoselectivity is the cycloaddition-aldol-retro-ene process depicted in scheme 20.1581 The procedure presumably starts with a [4+2]-cycloaddition of diene 98 and S02 in presence of a Lewis acid. After opening of the formed adduct reaction with (Z)-silyl vinyl ether 99 leads to a mixture of alk-2-enesulfinic acids 101. It follows a retro-ene reaction which affords a 7 3 mixture of the products 102 and 103. The reaction described by Vogel et al is a nice example for the efficient generation of polypropionate chains with the stereoselective formation of three stereogenic centers and one (0-double bond in a three-component domino reaction in its strict definition. 

Recent contributions from Vogel s group have shown that, under CO atmosphere and in the presence of Pd2(dba)3 and Ph3As, 1-stannyl glycals can be carbonylated and coupled to organic halides (Scheme 6a),38 or vinyl triflates (Scheme 6b),39 in carbonylative Stifle cross-coupling processes.40 Also of interest is the palladium catalyzed cross-coupling reaction of... 

Vogel TM, Reinhard M. 1986. Reaction products and rates of disappearance of simple bromoalkanes, 1,2-dibromopropane, and 1,2-dibromoethane in water. Environ Sci Technol 20 992-997. 

An excellent recent review of solvolysis reactions is to be found in Vogel P (1985) Carbocation Chemistry, Studies in Organic Chemistry, 21, Elsevier, Amsterdam... 

Chemical/Physical. Products of hydrolysis include chloroacetaldehyde, 1,1-dichloroethylene, and HCl. The aldehyde is subject to hydrolysis forming hydroxyacetaldehyde and HCl (Kollig, 1993). The reported half-life for this reaction at 20 °C is 170 yr (Vogel et al., 1987). Under alkaline conditions, 1,1,2-trichloroethane hydrolyzed to 1,2-dichloroethylene. The reported hydrolysis half-life in water at 25 °C and pH 7 is 139.2 yr (Sata and Nakajima, 1979). 

The synthetic breakthrough in cycloproparene chemistry was achieved by Anet and Anet in 1964 who prqtared l,l-dimethyl-3-methoxycarbonylbenzocyclo-propene (9) by irradiation of the substituted 3H-indazole 8. The parent benzocyclopropene (1) was obtained a year later by Vogel et al. by retro-Diels-Alder reaction (Aldw-Rickert cleavage) of 10. ... 

The rate increases with polyanion concentration, reaches a maximum, and then decreases with further increase in polyanion concentration [Morawetz and Vogel, 1969]. Retardation occurs for reactions between ions of opposite charge because the polymer attracts one ion but repels the other. 

Named organic reactions / Thomas Laue and Andreas Plagens translated into English by Claus Vogel.—2nd ed. p. cm. 

W. Holand, W. Vogel, K. Nauman, J. Gummel, Interface reactions between machinable bioactive glass-ceramics and bone, J. Biomed. Mater. Res. 19 (1985) 303-312. 

Vogel and Delavier (26) reported a synthesis of the 6-azabicyclo[3.2.2]nonane skeleton 130 using an intramolecular azide-alkene cycloaddition strategy (Scheme 9.26). When refluxed in xylene, the azide 126 underwent an intramolecular 1,3-dipolar cycloaddition with the internal alkene. Nitrogen extrusion and subsequent rearrangement led to a mixmre of compounds 128, 129, and 130. Reactions of azides with the double bond of dienes were also used in various total syntheses of alkaloids, and will be discussed later in Section 9.2.2. 

Vogel, E. and Natarajan, A.T. The relation between reaction kinetics and mutagenic action of monofunctional alkylating agents in higher eukaryotic systems Interspecies comparisons. IN deSerres, F.J. and Hollaender, A., eds. Chemical Mutagens Principles and Methods for Their Detection, Volume 7. New York Plenum Press. 1982. p. 295-336. 

Esters of arenesulfonic acids are prepared by reaction of the corresponding alcohol with the arenesulfonyl chloride in the presence of a basic reagent, which has the function of activating the alcohol and binding the hydrogen chloride. The reaction is often carried out with pyridine, which is used as solvent. In the procedure for tosylates of primary aliphatic alcohols, described in A.l. Vogel, A Textbook of Practical Organic Chemistry, an aqueous solution of sodium hydroxide is used. Esters of primary alcohols are formed more easily than secondary-alkyl esters, while tertiary alcohols cannot be esterified under the usual conditions. 

Hansel, A., Jordan, A., Holzinger, R., Prazeller, R, Vogel, W., Lindinger, W. (1995) Proton transfer reaction mass spectrometry online trace gas analysis at the ppb level. Int. J. Mass Spectrom. Ion Processes 149/150 609-619. 

In a more detailed study of this reaction, Rausch, Vogel, and Rosenberg determined optimum conditions for the synthesis of either XXVII or XXVIII (90). Ruthenocene has also been mercurated using glacial acetic acid as the solvent, but pure products could not be separated (88). 

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