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stephen aldehyde synthesis wikipedia jump to content main menu main menu move to sidebar hide navigation main page contents current events random article about wikipedia contact us contribute help learn to edit community portal recent changes upload file special pages search search appearance donate create account log in personal tools donate create account log in contents move to sidebar hide top 1 mechanism 2 sonn müller method 3 see also 4 references toggle the table of contents stephen aldehyde synthesis 8 languages العربية বাংলা deutsch فارسی français 日本語 nederlands 中文 edit links article talk english read edit view history tools tools move to sidebar hide actions read edit view history general what links here related changes upload file permanent link page information cite this page get shortened url switch to legacy parser print export download as pdf printable version in other projects wikimedia commons wikidata item appearance move to sidebar hide from wikipedia the free encyclopedia chemical reaction not to be confused with stevens rearrangement stephen aldehyde synthesis named after henry stephen reaction type organic redox reaction 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 sncl 2 hydrochloric acid hcl and quenching the resulting iminium salt r ch nh 2 cl with water h 2 o 1 2 during the synthesis ammonium chloride is also produced it is a type of nucleophilic addition reaction stephen aldehyde synthesis mechanism edit the following scheme shows the reaction mechanism stephen aldehyde synthesis reaction mechanism by addition of hydrogen chloride the used nitrile 1 reacts to its corresponding salt 2 it is believed that this salt is reduced by a single electron transfer by the tin ii chloride 3a and 3b 3 the resulting salt 4 precipitates after some time as aldimine tin chloride 5 hydrolysis of 5 produces a hemiaminal 6 from which an aldehyde 7 is formed substitutes that increase the electron density promote the formation of the aldimine tin chloride adduct with electron withdrawing substituents the formation of an amide chloride is facilitated 4 in the past the reaction was carried out by precipitating the aldimine tin chloride washing it with ether and then hydrolyzing it however it has been found that this step is unnecessary and the aldimine tin chloride can be hydrolysed directly in the solution 5 this reaction is more efficient when aromatic nitriles are used instead of aliphatic ones however even for some aromatic nitriles e g 2 cyanobenzoic acid ethyl ester the yield can be low 5 sonn müller method edit in the sonn müller method the intermediate iminium salt is obtained from reaction of an amide with phosphorus pentachloride 6 7 consequently it cannot be performed with acyclic enolizable amides as the resulting imidoyl chloride is unstable to self condensation 8 see also edit amide reduction nitrile reduction pinner reaction a similar reaction using alcohols or amines as the nucleophile and without the reduction generated esters carboximidates or orthoesters references edit williams jonathan w 1943 β naphthaldehyde organic syntheses 23 63 doi 10 15227 orgsyn 023 0063 stephen henry 1925 a new synthesis of aldehydes j chem soc trans 127 1874 1877 doi 10 1039 ct9252701874 wang zerong 2009 comprehensive organic name reactions and reagents 3 volume set john wiley sons hoboken new jersey pp 2659 2660 isbn 978 0 471 70450 8 rabinovitz mordecai 1970 chapter 7 reduction of the cyano group in rappoport zvi ed the cyano group 1970 patai s chemistry of functional groups john wiley sons ltd chichester uk p 308 doi 10 1002 9780470771242 ch7 isbn 978 0 470 77124 2 1 2 wang zerong 2009 comprehensive organic name reactions and reagents 3 volume set john wiley sons hoboken new jersey pp 2659 2660 isbn 978 0 471 70450 8 adolf sonn müller ernst 1919 über eine neue methode zur umwandlung von carbonsäuren in aldehyde about a new method for converting carboxylic acids into aldehydes berichte der deutschen chemischen gesellschaft a and b series 52 10 1927 1934 doi 10 1002 cber 19190521002 williams jonathan w witten charles h krynitsky john a 1946 o tolualdehyde organic syntheses 26 97 doi 10 15227 orgsyn 026 0097 mosettig e org react 1954 vol 8 p 241 doi 10 1002 0471264180 or008 05 retrieved from https en wikipedia org w index php title stephen_aldehyde_synthesis oldid 1367977645 categories organic redox reactions name reactions hidden categories articles with short description short description matches wikidata this page was last edited on 6 august 2026 at 08 44 utc page was rendered with parsoid text is available under the creative commons attribution sharealike 4 0 license additional terms may apply by using this site you agree to the terms of use and privacy policy wikipedia is a registered trademark of the wikimedia foundation inc a non profit organization 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