Amido-derivatives of metals and metalloids. Part IX. Reactions of tin(IV) and titanium(IV) amides with compounds having carbonyl and sulphinyl multiple bonds
- 1 January 1969
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society C: Organic
- No. 19,p. 2565-2568
- https://doi.org/10.1039/j39690002565
Abstract
Titanium(IV) and tin(IV) amides (reactivity: Ti > Sn) are useful reagents for some organic aminations. Reactions of R3Sn·NMe2(R = Me or Bun) or Ti(NMe2)4 with some carboxylic acids, anhydrides, amides, esters (alkyl, phenyl, enol, β-oxo, and αβ-unsaturated), and aldehyde, and acetone are reported. The following types were found: (i)(for most esters, CH2:1;CH·CO2H, and Ac2O), metathetical exchange with acyl–oxygen cleavage affording carboxylic acid amides; (ii)(for Me3Sn·NMe2 with CH2:1;CH·OAc), metathetical exchange with alkyl–oxygen fission; and (iii)(for Bun 3Sn·NMe2 with AcOH), protonolysis. Amination of sulphur dioxide with Ti(NMe2)4 afforded SO(NMe2)2, while methyl sulphoxides (MeSOR; R = Me or C6H11) were reductively aminated by the same reagent to afford Me2N·CH2SR.Keywords
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