Effect of the Catalyst Nature on the Structure of Products of the Reaction of 4-(Dibromomethyl)Benzaldehyde with Trialkyl Orthoformates
Reactions of 4-(dibromomethyl)benzaldehyde with trialkyl orthoformates in the presence of both Br?nsted (H2SO4) and Lewis (ZnCl2) acids involved acetalization of the aldehyde group. In the first case, the corresponding acetal is formed as the only product, whereas in the second case the reaction is accompanied by transformation of the dibromomethyl group to give terephthalaldehyde and its mono- and bis-acetals.
Gazizov,Ivanova, S. Yu.,Bashkirtseva, N. Yu.,Ibragimov, Sh. N.,Khairullin,Gazizova,Kostenko
p. 2783 - 2788
(2018/02/21)
Synthesis of functionally substituted benzaldehydes
A new method of synthesis of functionally substituted benzaldehydes by catalytic debromometoxylation of dibromomethylarenes with benzaldehyde dimethyl acetal has been suggested. Anhydrous zinc chloride has been used as a catalyst. Being soft Lewis acid, it formed no strong complex with aldehyde group and other functional groups. The initial acetal has been readily recovered by the treatment of benzaldehyde isolated from the reaction mixture with trimethyl orthoformate.
Gazizov,Ivanova, S. Yu.,Ibragimov, Sh. N.,Khairullin,Karimova,Gazizova,Antipin
p. 227 - 229
(2017/11/07)
The catalytic versatility of low toxicity dialkyltriazolium salts: In situ modification facilitates diametrically opposed catalysis modes in one pot
The ability of triazolium salts to serve as a precatalyst for both an acid and a powerful base/nucleophile (controlled by additives) has been exploited in a process characterised by a unique in situ catalyst modification strategy. The Royal Society of Chemistry 2013.
Myles, Lauren,Gathergood, Nicholas,Connon, Stephen J.
supporting information
p. 5316 - 5318
(2013/06/27)
Regioselectivity in arene-catalyzed reductive lithiation of acetals of chlorobenzaldehydes
The regioselectivity of arene-catalyzed reductive lithiation of acetals of chlorobenzaldehydes strongly depends on the form of lithium metal employed as a reducing agent. According to previous findings, naphthalene catalyzed reductions run in the presence of lithium powder (high Na content) led to competitive metalations of both aromatic carbon-chlorine and benzylic carbon-oxygen bonds. At variance with these results, naphthalene catalyzed reductions run in the presence of lithium wire (either high or low Na content) led to highly regioselective metalation of aromatic carbon-chlorine bonds. These results disclose new possibilities of selective applications of arene-catalyzed reductive lithiation reactions.
Azzena, Ugo,Dettori, Giovanna,Sforazzini, Giuseppe,Yus, Miguel,Foubelo, Francisco
p. 1557 - 1563
(2007/10/03)
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