154587-28-7Relevant academic research and scientific papers
1-Organosulfonyl-2-sila-5-piperazinones: Synthesis, molecular and crystal structure, and chemical transformations into 2-aminoacid derivatives
Shipov, Alexandr G.,Kramarova, Eugenia P.,Fang, Huntse,Arkhipov, Dmitry E.,Nikolin, Alexey A.,Bylikin, Sergey Yu.,Negrebetsky, Vadim V.,Korlyukov, Alexandr A.,Voronina, Natalia A.,Bassindale, Alan R.,Taylor, Peter G.,Baukov, Yuri I.
supporting information, p. 114 - 121 (2013/10/01)
The reaction of chloro(chloromethyl)dimethylsilane and hexamethyldisilazane with N-methylamides of N0-organosulfonyl-2-amino acids (1aee), the derivatives of N-mesylglycine (a), N-tosylglycine (b), Nnosylglycine (c), N-nosylalanine (d) and N-nosylleucine (e), affords new type of silacyclanes, 1-organosulfonyl-2- sila-5-piperazinones 2aee. The presence of very labile SieN bonds in compounds 2 can be utilised in a variety of synthetic applications. The hydrolysis of 2aee yields disiloxanes 3aee, which can be subsequently transformed into fluorosilanes, such as 4a, by the reaction with boron trifluoride. Ring-opening reactions of piperazinones 2b with 1-chloromethyl-2-pyrrolidone and acetyl bromide lead to previously unknown silyloxonium chloride 6b and silyloxonium bromide 8b, respectively, containing fragments of 2-amino acids as C,O-chelate ligands. Crystal structures of N-methylamide 1b, piperazinones 2a, d, e, disiloxanes 3c, e, fluorosilane 4a, silyloxonium chloride 6b and silyloxonium bromide 8b have been determined by X-ray diffraction study. The silicon atom in piperazinones and disiloxanes is tetracoordinated while compounds 4a, 6b and 8b contain pentacoordinated Si atoms. Crown Copyright.
