Distannoxane-catalyzed acetilization of carbonyls

Understanding the Acetalization Reaction Based on its Reaction Path Network

“…Acetalization of carbonyl compounds with diols is a useful method for protecting reactive carbonyl groups in organic synthesis . The acetalization reaction is represented by the following scheme, where this reaction proceeds under acidic conditions and is reversible.…”

“…Acetalization of carbonyl compounds with diols is a useful method for protecting reactive carbonyl groups in organic synthesis. [1][2][3][4][5][6] The acetalization reaction is represented by the following scheme, where this reaction proceeds under acidic conditions and is reversible. To obtain the product with a sufficient yield, it is necessary to remove the water, a byproduct of this reaction, using Dean-Stark apparatus.…”

Cobalt(II) schiff base functionalized mesoporous silica as an efficient and recyclable chemoselective acetalization catalyst

“…Acetals are commonly prepared from alcohol and/or corresponding trialkyl orthoformate with Brønsted and Lewis acid catalysts [20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35]. Although many efficient and reliable reactions for the conversion of carbonyl compounds to their corresponding acetals have been reported, there are, however, some drawbacks such as long reaction times, tedious work-up and separation of catalyst, toxic metal waste, unwanted side reaction and nonselectivity regarding these methods.…”

1,1,3,3-Tetrabutyl-1,3-diisothiocyanatodistannoxane

“…9 In addition to functioning to cleave acetals, distannoxane 1 can also catalyze acetalization of aldehydes (eq 6). 9 Optimization of 1-hexenal acetalization revealed that the activity of distannoxane catalyst could be increased through substitution of one of the thiocyanate groups for hydroxide: the half-life (t 1/2 ) of the reaction was lowered from 12.9 to 5.1 min. As a consequence, the scope and limitations of this reaction were developed using distannoxane 10.…”