AI Article Synopsis
- A series of metalloporphyrin dimers were synthesized as Tröger's bases or spiro-Tröger's bases using various substituted porphyrin derivatives.
- The process involved converting free-base porphyrins to metalloporphyrins and nitrating them, followed by reduction to produce β-aminometalloporphyrins, which were then reacted with methanal to yield different types of Tröger's bases.
- The yields and ratios of the products were influenced by factors such as the type of acid used, the equivalent of methanal, and the solvent, with chlorinated solvents being crucial for spiro-Tröger's base formation, confirmed through electron diffraction.
Article Abstract
A series of metalloporphyrin dimers as Tröger's bases or spiro-Tröger's bases was prepared starting from five different -symmetry porphyrin derivatives substituted in -positions by Ph, 3-MeO-Ph, 4-MeO-Ph, 3,4-(MeO)-Ph, or 3,5-(MeO)-Ph. Free-base porphyrins were converted to metalloporphyrins, which were subsequently nitrated with nickel(II), copper(II), or zinc(II) nitrate to give β-nitrometalloporphyrins. These were further reduced to β-aminometalloporphyrins and treated with a methanal equivalent under acidic conditions to selectively obtain Tröger's base , spiro-Tröger's base , or a mixture of both, in yields up to 41% of and 45% of depending on the reaction conditions used. The ratio of to was influenced by the methanal equivalent used, the strength of the acid, and, above all, the solvent. The presence of a metal ion within the porphyrin core and the use of a chlorinated solvent were found to be essential for the formation of spiro-Tröger's base . The molecular structure of spiroTB was proven by electron diffraction.
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| http://dx.doi.org/10.1021/acs.joc.2c01716 | DOI Listing |
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