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Dialkylation and methoxyalkylation of butadiene with diethyl malonate anions

✍ Scribed by Björn Åkermark; Anders Ljungqvist; Mauro Panunzio

Book ID
104235194
Publisher
Elsevier Science
Year
1981
Tongue
French
Weight
214 KB
Volume
22
Category
Article
ISSN
0040-4039

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✦ Synopsis

Butadiene has been transformed into diethyl 2,7-diethoxycarbonyl-4octenedioates and ethyl 2-ethoxycarbonyl-6-methoxy-4-hexenoates by reacting n-4-chloro-and 4-methoxybutenylpalladium complexes, respectively, with malonate anions.

The industrial production of adiponitrile via metal catalyzed 1,4-addition to butadiene2 and the preparation of 1,4_diacetoxybutene from butadiene and acetate 3 demonstrate the synthetic usefulness of 1,4-addition to 1,3-dienes. As recently shown by diamination of 1,3cyclohexadiene, this type of addition may be stereospecific. 4

In order to study the scope of 1,4-addition reactions we have investigated the 1,4-dialkylation and 1,4_methoxyalkylation of butadiene, in THF-solution, using malonates as alkylating agents. The exploratory experiments have utilized the r-allylcomplexes

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