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NHC-catalyzed reaction of enals with unactivated enones: substituent effect on the formation of 1 : 1 and 1 : 2 adducts

✍ Scribed by Takaki, Ken; Shiraishi, Kazuhiro; Okinaga, Kosuke; Takahashi, Shintaro; Komeyama, Kimihiro

Book ID
120379076
Publisher
The Royal Society of Chemistry
Year
2011
Tongue
English
Weight
378 KB
Volume
1
Category
Article
ISSN
2046-2069

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Anomalous formation of 1,1,4-tribromohex
Anomalous formation of 1,1,4-tribromohex-1-en-3-one in the wittig reaction of 2-halopent-2-enals with dibromomethylene triphenylphosphorane
✍ F. Camps; J. Coll; G. FabriΓ‘s; A. Guerrero; M. Riba πŸ“‚ Article πŸ“… 1983 πŸ› Elsevier Science 🌐 French βš– 232 KB

The heretofore unreported Wittig reaction of Z-halopent-Z-enals with dibromomethylene triphenylphosphorane yields variable amounts of 1,1,4-tribromohex-1-en-3-one and/or the expected dienes according to the substrate and reaction conditions. A plausible mechanism to rationalize the unforeseen format