Repozytorium

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

Xiaofang Li

Bin Liu

X. Yu

Pinggui Yi

R. Yi

Piotr J. Chmielewski

Rok wydania

2012

Czasopismo

Journal of Organic Chemistry

Numer woluminu

77

Strony

2431-2440

DOI

10.1021/jo3000817

Kolekcja

Naukowa

Język

Angielski

Typ publikacji

Artykuł

Streszczenie

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

Strona internetowa wydawcy

https://www.acs.org/content/acs/en.html