Novel amino propyl substituted organo tin compounds

Abstract

In this work, a new synthetic pathway yielding unprotected amino propyl tin compounds is described. For this purpose, mono stannanes with different substitution patterns are used. In a first step, tin hydrides are deprotonated using lithium diisopropyl amide and mixed with an electrophile containing a protected amine in the ω-position. After deprotection via acidic hydrolysis, the desired amino propyl tin compounds are obtained in high yield and purity. The thermal reaction behavior of the amino propyl tin hydrohalide intermediates containing one aromatic residue at the central tin atom is also investigated. For this purpose, amino propyl tin hydrohalides are heated under vacuum until the aromatic hydrocarbon is liberated. This thermal treatment leads to so far unknown tin halides containing an amino propyl side chain. For all of these substances detailed liquid 1H, 13C, and 119Sn-nuclear magnetic resonance (NMR) data were obtained, and in one case solid state NMR is also conducted. Regarding solids, single crystal X-ray analysis is performed. Some derivatization reactions with these new substances are demonstrated, especially the synthesis of an amino propyl tin carboxylate, which might be very interesting for biological, pharmaceutical, or technical processes.