ETD system

Electronic theses and dissertations repository

 

Tesi etd-05102007-160743


Thesis type
Tesi di dottorato di ricerca
Author
Signore, Giovanni
URN
etd-05102007-160743
Title
New Synthetic Approaches to Alk-1-enyl Sulfones and Sulfoxides
Settore scientifico disciplinare
CHIM/06
Corso di studi
SCIENZE CHIMICHE
Commissione
Relatore Prof. Menicagli, Rita
Parole chiave
  • Reissert-like reactions
  • organoalane-pyridine complexes
  • alk-1-enyl sulfoxides
  • alk-1-enyl sulfones
Data inizio appello
15/02/2007;
Consultabilità
completa
Riassunto analitico
This thesis is devoted to the finding of new synthetic approaches to alk-1-enyl sulfones and sulfoxides. In particular, uncomplexed organoaluminum reagents reacted with aluminium sulfinates to afford alkenyl sulfoxides in good yields (72-75%). Sulfonyl chlorides reacted with pyridine-complexed alanes in the presence of PPh3 to afford sulfoxides in up to 94% yields; a reasonable mechanism is proposed. Sulfinyl chlorides react with alkynyl aluminium reagents to give alkynyl sulfoxides in modest yields (43-57%). Pyridine-complexed organoalanes react with sulfonyl chlorides in the presence of Ph3PO to give alkenyl sulfones in good yields (75%). Uncomplexed organoalanes reacted with pyridine-sulfonyl chloride complexes to afford sulfones in variable yields (40-90%). Finally, N-acyl-2-alkenyl-2H-dihydropyridine and dihydroisoquinoline derivatives are obtained via reaction of organoalane-pyridine complexes with acid halides.