1,3-Dipolar Cycloaddition of 2,6-Dichlorobenzonitrile Oxide to 2-Methyl-N-confused Porphyrin. Regio- and Stereoselective Synthesis and Structural Characterization of 2-Aza-21-carbabacteriochlorin and

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• 作者：Xiaofang Li ; Bin Liu ; Xianyong Yu ; Pinggui Yi ; Rongqiong Yi ; Piotr J. Chmielewski
• 刊名：The Journal of Organic Chemistry
• 出版年：2012
• 出版时间：March 2, 2012
• 年：2012
• 卷：77
• 期：5
• 页码：2431-2440
• 全文大小：565K
• 年卷期：v.77,no.5(March 2, 2012)
• ISSN：1520-6904

文摘

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.