Cyclohexanamine, N-[2-(triethylsilyl)propylidene]-

Physical properties

bp 84–86°C/0.1 mmHg.

Toxicology

(α-Triethylsilyl)propionaldehyde Cyclohexylimine is a reagent used for the selective formation of (E)-α-methyl-α,β- unsaturated aldehydes. The anions of α-silyl aldimines have been used to prepare unsaturated aldehydes by means of Peterson alkenation reactions.4,5 The anions of α-trimethylsilyl- or α-triethylsilylpropionaldehyde t-butylimine are easily prepared by treatment of the silyl aldimine with LDA or s-butyllithium (eq 1).Condensation of the α-lithio species with aldehydes and ketones conveniently yields α,β-unsaturated aldehydes following hydrolysis of the intermediate unsaturated imines (eqs 2 and 3).

Preparation

(α-Triethylsilyl)propionaldehyde Cyclohexylimine is prepared from propionaldehyde Ncyclohexylimine1,2 by treatment with lithium diisopropylamide in THF at ?78°C for 30 min followed by the addition of chlorotriethylsilane and gradually warming to 0 °C over a 3–4 h period.

Raw materials

Preparation Products