Journal
JOURNAL OF PORPHYRINS AND PHTHALOCYANINES
Volume 20, Issue 8-11, Pages 997-1001Publisher
WORLD SCI PUBL CO INC
DOI: 10.1142/S1088424616500097
Keywords
expanded porphyrin; hexaphyrin; triphenylphosphine; phosphonium ylide; phosphorane
Categories
Funding
- MEXT of Japan [25220802(S)]
- Grants-in-Aid for Scientific Research [14J01050] Funding Source: KAKEN
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Triphenylphosphine was added regioselectively at the C(3) position of bis-Au(III) complex of [26] hexaphyrin 5 in the presence of trifluoroacetic acid to produce [28] hexaphyrin triphenylphosphine adduct 6 in 62% yield, which has been fully characterized by NMR, UV-vis/NIR absorption, and MS spectroscopies, and X-ray diffraction analysis. The rigid planar structure forces 6 to take Huckel antiaromaticity, which has been supported by its H-1 NMR spectrum. Curiously, the detailed structural analysis elucidated that the triphenylphosphine moiety exists as a phosphorane form in the solid state. A plausible mechanism via a double protonated 5 is proposed, which can explain the observed regioselectivity.
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