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(Alkenyl)(amino)carbene Complexes: Potential Starting Materials for the Synthesis of Cyclopropylacetic Acid Derivatives

✍ Scribed by Antonio Papagni; Stefano Maiorana; Emanuela Licandro; Raffaella Manzotti; Clara Baldoli

Publisher
John Wiley and Sons
Year
2001
Tongue
English
Weight
343 KB
Volume
2001
Category
Article
ISSN
1434-193X

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✦ Synopsis

The (δ-hydroxyalkenyl)(pyrrolidino)carbene complexes, prepared by means of aldol additions of the (propenyl)(pyrrolidino)carbene complex to p-nitrobenzaldehyde and 4-pyridinecarbaldehyde, have been treated with methyl N-(triethylammoniosulfonyl)carbamate inner salt (Burgess reagent) to afford the corresponding adducts in almost quantitative yields. Treatment of these adducts with NaOH in methanol gave the corresponding conjugated polyunsaturated (amino)carbene complexes in fair yields. Alternatively, heating the adducts to 55-60 °C led to the isolation of cyclopropylacetic acid de-

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