0000000001320966
AUTHOR
António Aguiar
1,3-Dipolar cycloadditions with meso-tetraarylchlorins – site selectivity and mixed bisadducts
The 1,3-dipolar cycloaddition reaction of meso-tetraarylporphyrins with nitrones gives isoxazolidine-fused chlorins. Depending on the substitution pattern on the meso-aryl groups and the nitrone, the chlorins can be obtained in high yields (up to 91%). Bacteriochlorin-type bisadducts are also obtained, although in low yield, from the reaction of meso-tetrakis(pentafluorophenyl)porphyrin with N-methyl, N-cyclohexyl or N-benzyl nitrone. The structure of a bis(N-benzyl isoxazolidine-fused) bacteriochlorin was determined by single-crystal X-ray diffraction and rationalized by DFT calculations. To further explore the nature of site selectivity in the formation of bisadducts, isomeric mixed bacte…
CCDC 1488184: Experimental Crystal Structure Determination
Related Article: José Almeida, António Aguiar, Andreia Leite, André M. N. Silva, Luís Cunha-Silva, Baltazar de Castro, Maria Rangel, Giampaolo Barone, Augusto C. Tomé, Ana M. G. Silva|2017|Org.Chem.Front.|4|534|doi:10.1039/C6QO00771F