Chemistry Heterocyclic Building Blocks Thiophenes dihydrothiophen-3(2H)-one
Nucleophilic Addition: Dihydrothiophen-3(2H)-one is susceptible to nucleophilic addition reactions at the carbonyl (C=O) group. This can involve various nucleophiles such as amines, hydride sources (e.g., NaBH4), and organometallic reagents (e.g., Grignard reagents). The outcome depends on the specific nucleophile and reaction conditions.
Oxidation: The sulfur atom in dihydrothiophen-3(2H)-one can be oxidized to give sulfoxides or sulfones when treated with strong oxidizing agents like hydrogen peroxide (H2O2) or peracids.
Reduction: The carbonyl group can be reduced to the corresponding alcohol using reducing agents like sodium borohydride (NaBH4) or lithium aluminum hydride (LiAlH4).
Acylation: Dihydrothiophen-3(2H)-one can undergo acylation reactions with acyl chlorides or anhydrides to form ketones or amides.
Ring-Opening Reactions: Depending on the reaction conditions, dihydrothiophen-3(2H)-one can undergo ring-opening reactions to give linear or branched products. This can occur under acidic or basic conditions.
Michael Addition: Dihydrothiophen-3(2H)-one can participate in Michael addition reactions with Michael acceptors, such as α,β-unsaturated carbonyl compounds, in the presence of a base. This leads to the addition of the thiolane-3-one to the double bond of the acceptor.
Substitution Reactions: The halogenation of dihydrothiophen-3(2H)-one can occur, which can lead to the substitution of the sulfur atom with a halogen (e.g., chlorine or bromine).
Heterocycle Formation: Dihydrothiophen-3(2H)-one can participate in the formation of other heterocyclic compounds by reaction with appropriate reagents, leading to the expansion or modification of the thiophene ring.
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