OZONOLYSIS OF OLEFINS .6. CYANOACETALDEHYDE BY OZONOLYSIS OF (E)-1,4-DICYANO-2-BUTENE OR ALLYL CYANIDE

A new route for the preparation of cyanoacetaldehyde (3-oxopropanenitrile, 1) and its stable dimethyl acetal (3,3-dimethoxypropanenitrile, 2), which both are valuable intermediates for organic synthesis, is described. It starts from (E)-1,4-dicyano-2-butene or allyl cyanide (3-butenenitrile), respec...

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Bibliographic Details
Published inSynthesis (Stuttgart) no. 3; pp. 275 - 276
Main Authors JACHAK, M, MITTELBACH, M, KRIESSMANN, U, JUNEK, H
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.03.1992
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
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Summary:A new route for the preparation of cyanoacetaldehyde (3-oxopropanenitrile, 1) and its stable dimethyl acetal (3,3-dimethoxypropanenitrile, 2), which both are valuable intermediates for organic synthesis, is described. It starts from (E)-1,4-dicyano-2-butene or allyl cyanide (3-butenenitrile), respectively, which are ozonized at -40-degrees-C and further treated with dimethyl sulfide to give a solution of 1. This solution can either be used directly for further reactions or be transformed into the dimethyl acetal 2. The overall yield of 2 is 67 to 71 %. The acetal can be hydrolyzed again by treatment with Amberlyst-15 to give 1.
ISSN:0039-7881