Hard Acid and Soft Nucleophile System. VII. A Convenient Reduction of Functionalized Polyarenes to Parent Polyarenes

• Published in: Chemical & pharmaceutical bulletin Vol. 31; no. 12; pp. 4306 - 4311
• Main Authors: NODE, MANABU, NISHIDE, KIYOHARU, KAWABATA, TAKEO, OHTA, KEIICHIRO, WATANABE, KHOJI, FUJI, KAORU, FUJITA, EIICHI
• Format: Journal Article
• Language: English
• Published: Tokyo The Pharmaceutical Society of Japan 1983; Maruzen; Japan Science and Technology Agency
• Subjects: Chemistry; Condensed benzenic and aromatic compounds; Exact sciences and technology; Organic chemistry; Preparations and properties; reductive displacement; Thiol; Ether; Hydrocarbon; Aluminium III Chlorides; Tricyclic compound; Condensed benzenic compound; Halocarbon; Organic sulfide; Chemical reduction; Bicyclic compound; Reaction mechanism; Dichloromethane; Phenols
• ISSN: 0009-2363; 1347-5223
• DOI: 10.1248/cpb.31.4306

Oxygen functions and halogens at the peri-carbon atom in polyarenes were reductively removed with the AlCl3-EtSH reagent system to afford the parent polyarenes in high yield. The reaction consists of two steps of reactions involving displacement of a functionality with an alkylthio group followed by reductive removal of the introduced alkylthio moiety. A radical cation induced mechanism for the latter process is proposed on the basis of several observations.