N-[(Tri-n-butylstannyl)methyl]benzaldimine

Abstract

[116360-40-8] C20H35NSn (MW 408.27) InChI = 1S/C8H8N.3C4H9.Sn/c1-9-7-8-5-3-2-4-6-8;3*1-3-4-2;/h2-7H,1H2;3*1,3-4H2,2H3; InChIKey = KZTZGHBKRRYEIY-UHFFFAOYSA-N (synthesis of 2-phenylpyrrolidines by [3 + 2] cycloaddition of the derived 2-azaallyl anion with alkenes;1, 2 related compounds allow synthesis of other 2-substituted, 2,2-disubstituted, 2,5-disubstituted, or 2,2,5-trisubstituted pyrrolidines or pyrrolines1-3) Physical Data: bp 145–155 °C/0.1 mmHg (Kugelrohr air bath). Solubility: freely sol common organic solvents. Form Supplied in: clear, colorless oil; not available commercially. Analysis of Reagent Purity: 1H NMR. Preparative Methods: prepared by Staudinger reaction between benzaldehyde, Triphenylphosphine, and (azidomethyl)tributylstannane [prepared from (iodomethyl)tributylstannane and Sodium Azide].2 A more convenient procedure for the preparation of similar stannanes by condensation of an aldehyde or ketone with (aminomethyl)tributylstannane has been developed.3 Related 2-azaallylstannanes such as 1-alkyl-, 1,1-dialkyl-, 1,3-dialkyl-, and 1,1,3-trialkyl-2-azaallylstannanes may also be prepared, particularly using the latter method. Handling, Storage, and Precautions: since tetraalkylstannanes in general are considered toxic,4 handling in a fume hood is recommended. The reagent is stable in a freezer for extended periods, but is easily hydrolyzed by aqueous acids, and is partially hydrolyzed by silica gel chromatography.