NEW SYNTHETIC APPROACHES TO ALK-1-ENYL SULFONES AND SULFOXIDES

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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.