Tellurobenzaldehyde by Staudinger‐Chalcogenation of the Ylide Benzylidenetriphenylphosphorane

Abstract

The ylide Ph3PCHPh 1 and elemental tellurium react at 105°C in toluene to afford in situ tellurobenzaldehyde 2. Compound 2 is trapped with 2,3-dimethylbutadiene to form 3 and reacts with 1 to give stilbene; 2 is the first telluroaldehyde to be prepared in free form. The authors suggest the term “Staudinger-chalcogenation” for this method of synthesis.