A facile two-carbon ring expansion process based on the 2-cyano-1-vinylcycloalkanol system

Metal-Mediated Reductive Hydrodehalogenation of Organic Halides

“…A series of o -fluorobenzamides 57 were reduced with LAH under mild reaction conditions to give the corresponding dehalogenated products 58 in a chemospecific manner and with moderate yields (Scheme ) . Chemo- and regioselective ortho -dehalogenation (F, Cl) was also observed when the aromatic ring also bore halogens (F, Cl) on the meta - or para -positions.…”

Cyclic Oxonitriles: Synergistic Juxtaposition of Ketone and Nitrile Functionalities

“…Ring expansion of a polysubstituted hydroxynitrile points to a sequential ringopening-Michael-addition mechanism in which the metalated nitrile 154 is the key intermediate. 147 The two-carbon ring expansion is equally effective for five-, six-, seven-, and twelve-membered b-oxonitriles having a variety of substituents. The nitrile is unique in promoting the reaction with the corresponding ester causing extensive degradation under comparable conditions.…”

Catalytic synthesis of seven-membered carbocycles via ring expansion of cyclic β-ketoesters

“…Among the established methods of making seven-membered rings, the five-to-seven ring expansion method is particularly charming since it provides a versatile, reliable, and predictable strategy affording medium-sized rings from normal and easily available five-membered ring compounds. 2 For instance, the Rh-catalyzed alkyne arylation–cyclization–ring opening sequence has been developed to make cycloheptanone (Scheme 1a). 2 a A [2+2] annulation-ring expansion method has been reported to afford cycloheptane-1,3-diones (Scheme 1b).…”