Home Chemistry Organic Building Blocks Aliphatic Cyclic Hydrocarbons Cyclopropoxybenzene
Electrophilic Aromatic Substitution (EAS): Cyclopropoxybenzene can undergo EAS reactions in which an electrophile substitutes a hydrogen atom on the benzene ring. Common electrophiles include halogens (e.g., Cl2, Br2), nitronium ion (NO2+), and alkylating agents. The cyclopropyl group can affect the regioselectivity of the substitution, leading to specific substitution patterns on the benzene ring.
Nucleophilic Aromatic Substitution (SNAr): If there are suitable leaving groups on the cyclopropyl ring or benzene ring, nucleophilic aromatic substitution reactions can occur. Nucleophiles such as amines, alkoxides, or thiols can replace a leaving group on the benzene ring or the cyclopropyl ring.
Reduction: The cyclopropyl ring in cyclopropoxybenzene can be reduced using reducing agents like lithium aluminum hydride (LiAlH4) or sodium borohydride (NaBH4
) to form cyclopropylmethanol.
Oxidation: Cyclopropoxybenzene can be oxidized using strong oxidizing agents to generate various functional groups. For example, oxidation with chromic acid (H2CrO4) can convert the cyclopropoxy group into a carbonyl group.
Ring-Opening Reactions: The strained cyclopropyl ring in cyclopropoxybenzene can undergo ring-opening reactions under certain conditions. For instance, treatment with strong acids or nucleophiles can lead to the cleavage of the cyclopropyl ring and the formation of open-chain compounds.
Grignard Reaction: Cyclopropoxybenzene can react with Grignard reagents (alkyl or aryl magnesium halides) to form a new carbon-carbon bond, resulting in the addition of an alkyl or aryl group to the benzene ring.
Friedel-Crafts Alkylation and Acylation: These reactions can be used to introduce alkyl or acyl groups onto the benzene ring of cyclopropoxybenzene using Lewis acid catalysts such as aluminum chloride (AlCl3).
Rearrangement Reactions: Depending on reaction conditions and the presence of other functional groups, rearrangement reactions like Wagner-Meerwein rearrangements may occur in the cyclopropoxybenzene molecule.
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1-(Chloromethyl)-3-cyclopropoxybenzene
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(S)-2-Amino-2-(4-cyclopropoxyphenyl)ethanol hydrochloride
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