Stephen aldehyde synthesis
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Not to be confused with Stevens rearrangement.
Stephen aldehyde synthesis, a named reaction in chemistry, was invented by Henry Stephen (OBE/MBE). This reaction involves the preparation of aldehydes (R-CHO) from nitriles (R-CN) using tin(II) chloride (SnCl2), hydrochloric acid (HCl) and quenching the resulting iminium salt ([R-CH=NH2]+Cl-) with water (H2O).[1]
Overall, the reaction scheme is as follows:
[edit] Sonn-Müller method
In the Sonn-Müller method [2] [3] the intermediate iminium salt is obtained from reaction of an amide PhCONHPh with phosphorus pentachloride.
[edit] References
- ^ Stephen, H. (1925). "A new synthesis of aldehydes". J. Chem. Soc., Trans. 127: 1874–1877. doi:.
- ^ Sonn and Müller, Ber., 52, 1929 (1919).
- ^ Jonathan W. Williams, Charles H. Witten, and John A. Krynitsky (1955). "o-Tolualdehyde". Org. Synth.; Coll. Vol. 3: 818.
