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Mechanism of Mukaiyama−Michael Reaction of Ketene Silyl Acetal: Electron Transfer or Nucleophilic Addition?

✍ Scribed by Otera, Junzo; Fujita, Yukihiro; Sakuta, Nobuyuki; Fujita, Morifumi; Fukuzumi, Shunichi

Book ID
120828014
Publisher
American Chemical Society
Year
1996
Tongue
English
Weight
599 KB
Volume
61
Category
Article
ISSN
0022-3263

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Mukaiyama-Michael reaction of cyclic ket
Mukaiyama-Michael reaction of cyclic ketene silyl acetals and enones. Importance of ring flexibility in electron transfer process
✍ Yukihiro Fujita; Shunichi Fukuzumi; Junzo Otera 📂 Article 📅 1997 🏛 Elsevier Science 🌐 French ⚖ 164 KB

Michael reaction of macrocyclic ketene silyl acetals or a-enones occurs smoothly under electron transfer conditions while the reaction of 6-membored analogs is more sluggish, indicating the importance of the ring flexibility to allow the a,~-carbon-carbon bonds of both reaction components to rotate