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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 resolution of 2-aza-21-carbachlorin enantiomers.
Autorzy
Rok wydania
2012
Czasopismo
Numer woluminu
77
Strony
2431-2440
DOI
10.1021/jo3000817
Kolekcja
Język
Angielski
Typ publikacji
Artykuł
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.
Adres publiczny
https://doi.org/10.1021/jo3000817