ABSTRACT
Aromatic fluorinated hydrocarbons, used as solvents for olefin metathesis reactions, catalysed by standard commercially available Ru precatalysts, allow substantially higher yields to be obtained, especially of challenging substrates, including natural and biologically active compounds.
Subject(s)
Alkenes/chemistry , Biology , Fluorine Compounds/chemistry , Hydrocarbons, Aromatic/chemistry , Solvents/chemistry , Biological Products/chemical synthesis , Biological Products/chemistry , Catalysis , Magnetic Resonance Spectroscopy , Molecular StructureABSTRACT
Molecular rearrangements consisting of base- or acid-induced dislocation of aromatic or heteroaromaticrings are reviewed. The emphasis is given to recent developments and, in particular, to synthetic applicationof the rearrangement. A novel classification has been applied in order to discuss systematically ratherdiverse published data. The rearrangements are reviewed according to atoms entering and leaving the ipso-position of the migrating ring. The Julia-Kocienski olefination reactionis presented in other parts of this volume.
ABSTRACT
Reaction of tosylhydrazones of O-substituted alpha-hydroxy or N-substituted alpha-amino aldehydes (2, 7, 11, 15, 17, and 20) with selected alpha-magnesio alkyl phenyl sulfones afforded the respective derivatives of allylic alcohols or allylic amines. 2,3-O-Isopropylidene-D-glyceraldehyde (1) was transformed into its tosylhydrazone (2) and then olefins 4a with retention of optical purity.