Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 77, Issue 5, Pages 2431-2440Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo3000817
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Funding
- National Natural Science Foundation of China [20971041, 21172066]
- Chinese Ministry of Education [210146]
- Hunan Provincial Education Department [09K081]
- Key Laboratory of Theoretical Chemistry and Molecular Simulation of Ministry of Education, Hunan University of Science and Technology [LKF0902, LKF0903]
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The 1,3-dipolar cycloaddition reaction of 2-methyl-N-confused porphyrin with 2,6-dichlorobenzonitrile oxide yielded four isomeric monoadducts of carbachlorin type and one diadduct of carbabacteriochlorin type. Two major carbachlorin products, constituting 82% of the monoadducts, were shown to be structural precursors of the unique 2-aza-21-carbabacteriochlorin. Enantiomers of the most abundant isomer of 2-aza-21-carbachlorin (55% of all carbachlorin products) have been resolved. The crystal structures of 2-aza-21-carbabacteriochlorin and the most abundant isomer of 2-aza-21-carbachlorin were characterized by X-ray diffraction.
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