Z-Vinylic higher order cyanocuprates, prepared from the corresponding Z-vinylic tellurides, react efficiently with hindered enones in THF/BF3-Et20 or in diethyl ether. In neat THF the hindered enones fail to react with Z-vinyl cyanocuprates prepared in this way.
Influence of the gegenion in the transmetalation reaction of vinylic tellurides with higher order cyanocuprates
✍ Scribed by André Chieffi; João V. Comasseto
- Publisher
- Elsevier Science
- Year
- 1994
- Tongue
- French
- Weight
- 273 KB
- Volume
- 35
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
Dilithium cyanocuprates R*LCu(CN)Li2 (L=2-Th, Me) react with vinylic tellurides of Z configuration, RCH=CHTeRl to give higher order vinylic cyanocuprates, [(RCH=CH)LCu(CN)Li2]. By changing the gegenion from lithium to magnesium [R2LCu(CN)LiMgBr or R2LCu(CN)(MgBr)2] the reaction gives cross -coupling products of Z configuration, RCH=CHR2 in good yields.
📜 SIMILAR VOLUMES
The treatment of isomeric vinylic tellurides 5-7with butyllithium in THF at -78 °C in the presence of a carbonyl compound such as benzaldehyde or cyclohexanone was studied High selectivity of the attack at the tellurium atom was observed. In most cases, the corresponding allylic alcohol was obtained
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