Chiral "basket handle" binaphthyl porphyrins: Synthesis, catalytic epoxidation and NMR conformational studies

Journal of Porphyrins and Phthalocyanines

Volumn 14, Issue 7, 2010, Pages 646-659

  Rose, Eric ^a   Gallo, Emma ^b   Raoul, Nicolas ^a   Bouché, Léa ^a   Pille, Ariane ^a   Caselli, Alessandro ^b   Lequin, Olivier ^a  

^a SORBONNE UNIVERSITÉ   (France)

^b UNIVERSITY OF MILAN   (Italy)

Author keywords

binaphthyl porphyrin; chiral porphyrin; conformational exchange; enantioselective epoxidation; NMR

Indexed keywords

EID: 77957340036     PISSN: 10884246     EISSN: None     Source Type: Journal    
DOI: 10.1142/S1088424610002483     Document Type: Article

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71. The frst observation is the similar chemical shifts for the αβαβC2 and αβαβC3 porphyrin protons (Table 1). However for the αβαβC1 porphyrin, the chemical shifts of the H4' and H8' deserve comments. Indeed, the H4' protons resonate at a downfeld chemical shift of 8.36 ppm and are deshielded by 1.00 ppm with respect to the corresponding protons in αβαβC2 and αβαβC3. This can be explained by an anisotropy effect of the amido group directly linked to the naphthyl residue whereas in the other cases the naphthyl moiety is linked to a methylene group. For the signal of the H8' proton at 6.00 ppm, the effect of the anisotropy of the macrocycle shields it by a value of 2.11 ppm. The shieldings Δ8 for the two other porphyrins are 1.43 ppm for αβαβC2 and 1.22 ppm for αβαβC3.
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