1104076-75-6Relevant academic research and scientific papers
Reverse Kocheshkov reaction - Redistribution reactions between RSn(OCH2CH2NMe2)2Cl (R = Alk, Ar) and PhSnCl3: Experimental and DFT study
Portnyagin, Ivan A.,Lunin, Valery V.,Nechaev, Mikhail S.
, p. 3847 - 3850 (2008)
A series of organotin compounds bearing two intramolecular N → Sn coordination bonds RSn(OCH2CH2NMe2)2Cl (R = Me (4), n-Bu (5), Mes (6)) were synthesized in good yields. These compounds as well as 2 (R = Ph) react with PhSnCl3 to give redistribution products RPhSnCl2 and (Me2NCH2CH2O)2SnCl 2 (3). The direction of redistribution reactions is reverse to Kocheshkov reaction. DFT calculations have shown that the driving force of the reactions is formation of intramolecular N → Sn coordination bonds in (RO)2SnCl2 (3), the Lewis acid stronger than RSn(OR)2Cl (2, 4-6). The mechanism of the redistribution reaction between 2 and PhSnCl3 consists of two steps: (1) initial exchange of OCH2CH2NMe2 and Cl to give PhSn(OCH2CH2NMe2)Cl2 (7) followed by (2). Ph and OCH2CH2NMe2 exchange.
