Synthesis of bis-3,4-dialkoxythiophenes linked by am-xylene bridge

Two examples of bis 3,4-dialkoxythiophenes linked with am-xylene bridge were synthesized in yields of18% and 32% in a six step process. The formation of them-xylene bridge, key reaction of the synthesis,was carried out through Williamson, Mitsunobu andtrans-etherification reactions which were subse-quently compared on performance and versatility. The Mitsunobu reaction assisted by sonication wasfound to be the best strategy. These molecules are among the few examples of unsymmetrically substi-tuted 3,4-dialcoxythiophenes. During the synthesis an 18 member heterocycle, closely related to a crownether was isolated. The details of the XRD structure of this heterocycle are discussed.

• Egile nagusia: Cisneros Pérez, Pablo A. (author)
• Beste egile batzuk: Frontana Uribe, Bernardo A. (author), Martínez Otero, Diego (author), Cuevas Yáñez, Erick (author)
• Formatua: article
• Argitaratua: 2016
• Gaiak: 3,4-Dialkoxythiophene; m-Xylene bridge; Unsymmetrical etherification; Ultrasound; p-Conjugated systems
• Sarrera elektronikoa: http://repositorio.ikiam.edu.ec:8080/jspui/handle/RD_IKIAM/169; http://repositorio.ikiam.edu.ec/jspui/handle/RD_IKIAM/169; https://doi.org/10.1016/j.tetlet.2016.10.015