144730-20-1Relevant articles and documents
Synthesis of Methylenebicyclo[3.2.1]octanol by a Sm(II)-Induced 1,2-Rearrangement Reaction with Ring Expansion of Methylenebicyclo[4.2.0]octanone
Takatori, Kazuhiko,Ota, Shoya,Tendo, Kenta,Matsunaga, Kazuma,Nagasawa, Kokoro,Watanabe, Shinya,Kishida, Atsushi,Kogen, Hiroshi,Nagaoka, Hiroto
, p. 3763 - 3766 (2017)
Direct conversion of methylenebicyclo[4.2.0]octanone to methylenebicyclo[3.2.1]octanol by a Sm(II)-induced 1,2-rearrangement with ring expansion of the methylenecyclobutane is described. Three conditions were optimized to allow the adaptation of this approach to various substrates. A rearrangement mechanism is proposed involving the generation of a ketyl radical and cyclopentanation by ketyl-olefin cyclization, followed by radical fragmentation and subsequent protonation.
Radical Cyclization of Epoxyketones via a 1,5-Bun3Sn Group or a 1,5-H Atom Transfer
Kim, Sunggak,Koh, Jae Suk
, p. 1377 - 1378 (2007/10/02)
Radical cyclization of epoxyketones is initited by Bun3Sn radical addition to epoxyketones, followed by epoxide fragmentation, 1,5-H- or 1,5-Bun3Sn transfer, and cyclization.
