RESUMEN
A new family of thiophene-fused thiopyrylium salts has been synthesized via Lewis-acid-induced Rieche formylation, followed by an intramolecular Friedel-Crafts cyclization of a series of diarylthioethers. Moreover, in the case of diarylthioethers that bear formyl groups, Lewis-acid-promoted intramolecular cyclizations afforded novel thiophene-fused bisthiopyrylium salts in good yield. The electronic structures of the new compounds were determined experimentally by NMR and UV-vis absorption spectroscopy and theoretically investigated by density functional theory calculations. The results of our examinations revealed effective conjugation of the π-electrons over the entire linearly fused heteroacene framework.
RESUMEN
We observed that first delivery was delayed when a group of paired mice fed with non-organic common rice compared to a group fed with organic rice. This led us to hypothesize that pesticides or other soil contaminants may be responsible for the effect on mice reproduction. We then found that the non-organic rice was contaminated with a pesticide etofenprox and nonylphenol, butylphenol and diethyl phthalate which are used as agricultural detergents or plasticizers of agricultural film, that are all suspected to be estrogenic. Therefore, the chemicals were administered to mice at the levels detected in rice, and we subsequently observed that first delivery and sperm count of the animals were significantly impaired. This study is the first to show that rice contaminated with agricultural chemicals affects reproduction in the mammal.