Houben

Publications of this kind are described as non-original. They are abstracting services and handbooks that catch the primary literature, condense the important contents, and make this information available (searchable). Secondary literature is not evaluated and is provided in both printable and electronic forms. Examples are Gmelin, Beilstein, Citations Chemisches Zentralblatt, Chemical Abstracts, or Science Citation Index handbooks include Houben-Weyl, and Landolt Bomstein. 

Houben-Weyl, Die Methoden der organischen Chemie, Third Edition, Four Volumes, 1925-1941 Fourth Edition, Volume VIII, 1952 Volume n, 1953 and subsequent volumes (G. Thieme, Stuttgart). 

To explain the experimentally observed high reactivity of HCN and alkyl nitriles under snperacidic condition, Shndo found that in the Gat-terman and Houben-Hoesch reactions, diprotonated HCN (or nitriles) are involved as the de facto reagents (HC N H2, RC N H2). 

Criegee, R. Kropf, H. 1979, in Houben-Weyl, Methoden der Organischen Chemie, Vol. Vl/1 a-1 Alkohole I, p. 592, Thieme Stuttgart... 

E. Eorche, "Houben-Weyl, Methoden der Organischen Chemie," ia E. MueUer, ed., Halogen-Verbindungen, Georg Thieme Vedag, Stuttgart, 1962, pp. 1—502. R. EiUer, ia J. C. Tatiow, R. D. Peacock, and H. H. Hyman, ds.. Advances in Fluorine Chemisty, Vol. 6, CRC Press, Cleveland, Ohio, 1970, p. 1. 

Friedel-Crafts acylation using nittiles (other than HCN) and HCI is an extension of the Gattermann reaction, and is called the Houben-Hoesch reaction (120—122). These reactions give ketones and are usually appHcable to only activated aromatics, such as phenols and phenoHc ethers. The protonated nittile, ie, the nitrilium ion, acts as the electrophilic species in these reactions. Nonactivated ben2ene can also be acylated with the nittiles under superacidic conditions 95% trifluoromethanesulfonic acid containing 5% SbF (Hg > —18) (119). A dicationic diprotonated nittile intermediate was suggested for these reactions, based on the fact that the reactions do not proceed under less acidic conditions. The significance of dicationic superelectrophiles in Friedel-Crafts reactions has been discussed (123,124). 

R. Kitster, Houben-WeylMethoden der Organischen Chemie, Vol. Xlll/3a, 3b, 3c, G. Thieme, Stuttgart, Germany, 1982—1984. 

H. Hagemann, Houben-Weyh Koh/ensaure-Deripate, G. Thieme, New York, 1983. 

U. SchoUkopf, ia Houben/ WeylMethoden der Organischen Chemie, Series IV, Vol. 13/1, Thieme-Vedag, Stuttgart, Germany, 1970, p. 93. 

E. MbUer, ed., Methoden der Organischen Chemie (Houben-Weyl), Vol. IV/lb, Georg Thieme Vedag, Stuttgart, Germany, 1975. 

Houben-Weyl, Methoden der organischen Chemie, Vol. 2, 4th ed., John Wiley Sons, Inc., New York, 1944, pp. 178—224. 

J. Houben, ed.. Die Methoden der Organischen Chemie (Weyls Methoden), Georg Thieme Verlag, Stuttgart, Germany, 1925—1941 (reproduced by Edwards Bros., Inc., Ann Arbor, Mich.). 

HOUBEN - HOESCH Phenol Acylation Synthesis ol ketones (or aldehydes) by acylation ol phenols with nitriles (or ortho formates)... 

E. Wiinsch, Blockierung und Schutz der a-Amino-Function, in Methoden der Or-ganischen Chemie (Houben-Weyl), Georg Thieme Verlag, Stuttgart, 1974, Vol. 15/1, pp. 164-203, 250-264. 

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