10.2 Sulfur-Containing Compounds

Sulfur-containing compounds find wide applications in organic synthesis. This lecture covers some of the importance processes.

10.2.1 Reactions with Carbonyl Compounds

10.2.1.1 Julia Olefination (Julia-Lythgoe Olefination)

Aldehydes as well as ketones undergo reaction with sulfone having α -H in the presence of base to give an adduct which could be treated with acetic anhydride to afford acetyl derivative that could proceed reductive elimination in the presence of sodium amalgam to form alkene (Scheme 1). One of the important characteristics of this reaction is its high stereoselectivity for ( E )-disubstituted alkenes.

Mechanism

Scheme 1

10.2.1.2 Julia Coupling

Sulfones having α -hydrogen can be coupled with aldehydes using base (Scheme 2).

Scheme 2

Examples