Acyl iodides in organic synthesis: XII. Reactions with organosilicon amines

Abstract

Reactions were investigated between acyl iodides RCOI (R = Me, Ph) and organosilicon amines of two classes: trimethyl(diethylamino)silane, dimethyl-bis(diethylamino)silane, and hexamethyldisilazane on the one hand, and 3-aminopropyl(triorganyl)silanes H2N(CH2)3SiX3 (X = Et, EtO) on the other hand. The reaction of RCOI with trimethyl(diethylamino)silane Me3SiNEt2 occurred with a cleavage of the Si-N bond and the formation of N,N-diethylacet- or -benzamides and trimethyliodosilane separated in a mixture with hexamethyldisiloxane. At the reaction of acyl iodides RCOI (R = Me, Ph) with dimethyl-bis(diethylamino)silane in the ratio 2:1 in benzene solution both Si-N were ruptured leading to the diethylamide of the corresponding acid and dimethyldiiodosilane. The main product of the reaction of acetyl iodide with hexamethyldisilazane at the molar ratio 2:1 was diacetylimide (MeCO)2NH. This reaction can be recommended as a simple and convenient preparation procedure for diacylimides. The exothermal reaction of the acetyl iodide with 3-aminopropyl(triethyl)- and -(triethoxy)silanes at the molar ratio of the reagents 1:1 without solvent resulted in quaternary ammonium salts, hydroiodides of the corresponding acetylamides I−MeCON+H2(CH2)3SiX3 (X = Et, OEt).