A synthesis of cis-α-unsaturated nitriles by kinetically controlled decarboxylation
✍ Scribed by John Fairhurst; David C. Horwell; Graham H. Timms
- Book ID
- 104224427
- Publisher
- Elsevier Science
- Year
- 1975
- Tongue
- French
- Weight
- 120 KB
- Volume
- 16
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
The Doebner condensation of aldehydes with cyanoacetic acid gives a cis/trans mixture of a,B-unsaturated nitriles containing a high proportion of the trans isomer'. The purification of the minor c%s isomer has been accomplished by Inefficient and laborious fractional distillation or crystallisation'~'. However, Knoevenagel reaction gives the intermediate a-cyano-acrylic acids in high yicld'r3. It has been suggested4 that in these compounds the carboxylic acid group lies exclusively bans to the
📜 SIMILAR VOLUMES
It has been shown that over-all conversions of carbonyl compounds to olefins, similar to the well known "Wittig" reaction, could be effected using silicon-substituted carbanions 1 . Recently, an alkyl lithiomethylacetate was reported to be an excellent reagent for the synthesis of a,%-unsaturated ca
Diphenyl cyanomethylenephosphonate (PhO)2POCH2CN was prepared as a stable crystalline solid in high yield in a single step from acetonitrile, LDA, and (PhO)2P(O)C1. The potassium ylide generated from this compound afforded o;//-unsaturated nitriles upon reacting with aldehydes, with a stereoselectiv