Orthoamide, LXIV [1]. Aromatenformylierungen mit Tris(dichlormethyl)amin und Oligoformylamin-Derivaten in Gegenwart von Supersäuren / Orthoamides, LXIV [1]. Formylation of Aromatic Compounds by Tris(dichloromethyl)amine and Oligoformylamine Derivatives in the Presence of Superacids

Autor:	Willi Kantlehner, Ralf Kreß, Jean Sommer, Sylvia Leonhardt, Georg Ziegler, Alain Goeppert, Oliver Scherr
Rok vydání:	2007
Předmět:	Tris chemistry.chemical_compound Chemistry Organic chemistry Amine gas treating General Chemistry Formylation
Zdroj:	Zeitschrift für Naturforschung B. 62:995-1014
ISSN:	1865-7117 0932-0776
DOI:	10.1515/znb-2007-0803
Popis:	Tris(dichloromethyl)amine (4), triformamide (1) and tris(diformylamino)methane (“formylaalen”) (2) can be activated by addition of trifluoromethanesulfonic acid. The formylating systems thus formed transform activated aromatic compounds, such as toluene, anisole or 2,4- dimethoxybenzene to the corresponding aldehydes. The formylating ability of systems from 4 and superacids, such as FSO3H, FSO3H/SbF5, C4F9SO3H, and mixtures of aluminum chloride with C4F9SO3H and chlorosulfonic acid, respectively, is compared. In general, low reaction temperatures (−20 to −10 °C) are necessary to obtain aldehydes with acceptable to good yields. Remarkably, at higher temperatures (~ 100 °C) compound 4 can also act as a formylating agent in the presence of suitable zeolites, as e. g. zeolite HBEA. Reaction mechanisms of the new formylation reactions are proposed.
Databáze:	OpenAIRE
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