Allyl sulfoxides as precursors for radical two-carbon ring expansion of cyclobutanones
The two-carbon ring expansion of cycloalkanones is now possible in a two-step procedure. This procedure is based on an unusual cascade reaction that consists of a [2,3]-sigmatropic rearrangement (Mislow-Braverman-Evans rearrangement) of an allylic sulfoxide followed by a radical fragmentation-cyclization process (see scheme; AIBN = azobisisobutyronitrile).
Chuard, Rachel,Giraud, Anne,Renaud, Philippe
p. 4323 - 4325
(2007/10/03)
Mercurinium ion mediated ring expansion of 1-alkenyl-1-cycloalkanols
TMS ethers of 1-alkenyl-1-cycloalkanols readily rearranged to the ring expanded β-mercurio cycloalkanones via mercurinium ions, which could be converted into α-methylene cycloalkanones through elimination and further one carbon expanded cycloalkanones via
Kim,Uh
p. 4325 - 4328
(2007/10/02)
Ring Construction by Zirconium-promoted Reductive Coupling of Nitriles with Alkenes
Intramolecular reductive coupling of nitrile with alkene units in the presence of zirconocene prepared from (C5H5)2ZrCl2 and BuLi gives cyclic ketones; the intermediary metallacycle prepared from the 2-cyano-N-allylaniline derivative is very reactive and
Mori, Miwako,Uesaka, Noriaki,Shibasaki, Masakatsu
p. 1222 - 1224
(2007/10/02)
Transformations of α,α-Dichlorocyclopentanones Obtained by Three-Carbon Annelation
α,α-Dichlorocyclopentanones and α,α-dichloro-β-cyclopentanones, readily available by three-carbon annelation, are cleanly transformed under mild conditions via α-chloro enolates and α-chloro enones to a variety of alkylated and nonalkylated ketones and enones.
Depres, Jean-Pierre,Greene, Andrew E.
p. 2036 - 2037
(2007/10/02)
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