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Photochemical ring contraction of 1-aryl-1,4-dihydropyrazine to 1-aryl-1H-imidazole

Paper ID Volume ID Publish Year Pages File Format Full-Text
26894 43985 2013 6 PDF Available
Title
Photochemical ring contraction of 1-aryl-1,4-dihydropyrazine to 1-aryl-1H-imidazole
Abstract

•The 1-aryl-1,4-dihydropyrazines are unstable under irradiation with UV light.•The 1-aryl-1,4-dihydropyrazines undergo photochemical ring contraction to 1-aryl-1H-imidazoles.•The photochemical ring contraction is proposed to occur through a 6 π-electron cyclisation and a [1 + 2] cycloreversion.

The photochemical properties of 1-aryl-1,4-dihydropyrazines, including their UV–vis absorption, photostability and photoreaction, are investigated. The photostability of the 1-aryl-1,4-dihydropyrazines is studied in conventional solvents, and the results demonstrated that the 1-aryl-1,4-dihydropyrazines are unstable under irradiation with UV light. The 1-aryl-1,4-dihydropyrazines undergo photochemical ring contractions to 1-aryl-1H-imidazoles, as determined by 1H NMR, 13C NMR, HRMS, and single crystal X-ray diffraction analyses. The photochemical ring contraction is proposed to occur through a 6 π-electron cyclisation and a [1 + 2] cycloreversion.

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Keywords
1-Aryl-1,4-dihydropyrazine; Photochemistry; 1-Aryl-1H-imidazole; Ring contraction
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Photochemical ring contraction of 1-aryl-1,4-dihydropyrazine to 1-aryl-1H-imidazole
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Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology A: Chemistry - Volume 267, 1 September 2013, Pages 49–54
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering
Get Full-Text Now
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Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
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Any Questions? feel free to contact us