Synthesis and characterization of (4S)-1-chloroalkylsilatrane-4-carboxylic acids; cruytal structures of (3R,4S)-1-chloromethyl-3-methylsilatrane-4-carboxylic acid and (3R,4S)-1-(3-chloropropyl)-3-methylsilatrane-4-carboxylic acid

• Published in: Journal of organometallic chemistry 1995-03, Vol.489 (1), p.C38-C43
• Main Authors: Zheng-Rong Lu, Ren-Xi Zhuo, Liao-Rong Shen, Xiao-Dong Zhang, Lian-Fang Shen
• Format: Article
• Language: English
• Subjects: Silatrane compounds; Silicon
• ISSN: 0022-328X; 1872-8561
• DOI: 10.1016/0022-328X(94)05333-7

(4S)-1-(chloromethyl)silatrane-4-carboxylic acid 1 and (3R,4S)-1-chloromethyl-3-methylsilatrane-4-carboxylic acid 2 were synthesized by the transesterification of chlormethyltriethoxysilane with l -N,N- bis(2- hydroxyenthyl) serine or l -N,N- bis(2- hydroxyethy) threonine in teh presence of pyridine. (4S)-1-(3-chloropropyl)silatrane-4-caroxylic acid 3 and (3R,4S)-1-(3-chloropropyl)-3-methylsilstrane-4-carboxylic acid 4 were similarly synthesized from the reaction of 3-chloropropyltrimethoxysilane with the chiral ligands. The compounds were characterized by elemental analyses, IR spectra, 1H and 13C NMR spectra and mass spectra. The structures of compounds 2 and 4 were determined by X-ray single crystal diffraction. It is shown that the silatrynyl carboxylic acids are linked by the intermolecular hydrogen bonds to give linear polymer in the crystals, and the equatorial SiO oxygens behave as proton acceptor. It seems that the influence of the carboxylic group on teh SiN dative bond of compoung 4 is greater than that of compound 2.