107408-29-7Relevant articles and documents
Lithium-Halogen Exchange-Initiated Cyclization Reactions. 3. Intramolecular Conjugate Addition Reactions of Unsaturated Acylphosphoranes
Cooke, Manning P.,Widener, Rexford K.
, p. 1382 - 1396 (2007/10/02)
The lithium-halogen exchange-initiated intramolecular conjugate addition reactions of some model unsaturated acylphosphoranes have been examined.The effects of halide type, chain length, and acceptor substitution pattern on the feasibility of ring construction were studied.The lithium-bromine exchange reactions in two 2-bromooaryl acceptors were found to be too slow, relative to competing side reactions, to allow practical carbocycle syntheses while 3-,4-,5-, and 6-membered carbocycles are formed in good to excellent yields from precursors that are vinyl and saturated primary iodides.Highly efficient intramolecular conjugate addition reactions to β,β-disubstituted acceptor units are possible, and intermediate anions from intramolecular conjugate addition reactions are readily captured with electrophiles.