33766-66-4Relevant academic research and scientific papers
Stereochemistries and mechanisms of reactions of electrophiles with organotin compounds
Fukuto, Jon M.,Newman, David A.,Jensen, Frederick R.
, p. 415 - 420 (2008/10/08)
The effect of solvent and electrophile on halodemetalation reactions of carbon-tin bonds has been investigated. Both stereochemical results and 119Sn NMR have been used as mechanistic probes. The effect of solvent is extreme; reactions performed in polar solvents such as acetonitrile and dimethylformamide yield cleavage products with predominantly inversion of configuration, whereas nonpolar solvents yield products with predominantly retention. Polar-aprotic solvents appear to be highly efficient in promoting inversion stereochemistry. Polar-protic solvents are not as efficient. This is explained in terms of some very specific solvation phenomena. Also, 119Sn NMR studies of several trialkyltin halides in various solvents show that these specific solvation phenomena can be qualitatively assessed. The nature of the electrophile also plays an important role in eventual stereochemistry; Br2, I2, ICl, and IBr are compared and discussed.
