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Stephen aldehyde synthesis

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Title: Stephen aldehyde synthesis  
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Subject: Aldehyde, Nitrile, List of organic reactions, Iminium
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Stephen aldehyde synthesis

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] During the synthesis, ammonium chloride is also produced.

Overall, the reaction scheme is as follows:

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.


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