Cis–trans isomerization of dimethyl 2, 3-dibromofumarate. Issue 50 (14th November 2022)

• Record Type: Journal Article
• Authors: Vo, Timothy H.; Korlacki, Rafał; Sinitskii, Alexander
• Is Part Of: RSC advances. Volume 12:Issue 50(2022)
• Page Start: 32471
• Page End: 32474
• Publication Date: 2022-11-14
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/d2ra05996g
• Languages: English
• ISSNs: 2046-2069

Abstract

Abstract : The bromination of dimethyl acetylenedicarboxylate initially results in mostly trans dimethyl 2, 3-dibromofumarate, which then converts into the more stable cis isomer. The trans -to- cis conversion is spontaneous and greatly accelerated by light. Abstract : The isomerization of dimethyl 2, 3-dibromofumarate in chloroform solutions was investigated by the combination of nuclear magnetic resonance (NMR) and density functional theory (DFT) calculations. The bromination of dimethyl acetylenedicarboxylate leading to dimethyl 2, 3-dibromofumarate produces the trans isomer initially, which however converts into the more stable cis isomer. The conversion from trans to cis is spontaneous and greatly accelerated by light.