Shetti, Vijayendra S. ; Prabhu, Uday R. ; Ravikanth, Mangalampalli (2010) Synthesis and studies of thiacorroles The Journal of Organic Chemistry, 75 (12). pp. 4172-4182. ISSN 0022-3263
Full text not available from this repository.
Official URL: http://pubs.acs.org/doi/abs/10.1021/jo100607t
Related URL: http://dx.doi.org/10.1021/jo100607t
Abstract
The first examples of stable 22-thiacorroles containing a direct pyrrole−pyrrole bond were synthesized using thiophene monocarbinols as key precursors. Condensation of 1 equiv of thiophene monocarbinol with 1 equiv of substituted aldehyde and 1.5 equiv of pyrrole under refluxing propionic acid conditions followed by alumina column chromatographic purification yielded the desired 22-thiacorroles. Although the corrole formation had been observed with variety of substituted aldehydes, the stable thiacorroles were isolated in 2−3 % yields only with 4- and 3-nitrobenzaldehydes. The stable thiacorroles were obtained only under harsh propionic acid conditions and any other mild reaction conditions did not yield 22-thiacorroles. The structure of thiacorroles were unambiguously established using mass and 1D and 2D NMR spectroscopy. The NMR study indicated diminished ring current and distortion of 22-thiacorroles. DFT studies also supported the distortion of thiacorroles. The absorption spectra showed reduction in number of absorption bands and fluorescence study indicated that 22-thiacorroles are weakly fluorescent. The electrochemical studies indicated that 22-thiacorroles undergo easier reductions compared to thiaporphyrins.
Item Type: | Article |
---|---|
Source: | Copyright of this article belongs to American Chemical Society. |
ID Code: | 104594 |
Deposited On: | 30 Nov 2017 12:32 |
Last Modified: | 30 Nov 2017 12:32 |
Repository Staff Only: item control page