A microwave-assisted and efficient reduction protocol for the synthesis of alkyl-substituted [2.2]-paracyclophanes. Issue 2 (April 2023)

• Record Type: Journal Article
• Authors: Tian, Mengyuan; Zhang, Lixiang; Gao, Lijing; Xiao, Guomin
• Is Part Of: Journal of chemical research. Volume 47:Issue 2(2023)
• Publication Date: 2023-04
• Subjects: acylation -- microwave-assisted method -- parylene -- reduction -- 4-n-propyl-[2.2]-paracyclophane; Chemistry -- Research -- Periodicals; Chemistry -- Periodicals; 540.5
• DOI: 10.1177/17475198231164370
• Languages: English
• ISSNs: 1747-5198

Abstract

[2.2]-Paracyclophane derivatives have been promising platforms for applications in biology and materials science. To access pure derivatives thereof, a safe and non-toxic synthetic method for 4- n -propyl-[2.2]-paracyclophane is developed via a microwave-assisted and NH2 NH2 /KOH reduction route. We introduce microwave-assisted acylation for a synthesis that successfully improves the yield and reduces the reaction time. Notably, an exploration of the length and number of the alkyl chains on the [2.2]-paracyclophane ring did not significantly affect the outcome of this reaction. We synthesized 4- n -butyl-[2.2]-paracyclophane and 4, 12-dipropyl-[2.2]-paracyclophane via our protocol with high yields. The regioselectivity of the second electrophilic substitution on 4- n -propyl-[2.2]-paracyclophane occurs at the para position of the less substituted phenyl ring.