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Updated: Nov 30, 2025

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Naphtho- and anthra-disilacyclobutadienes
Shintaro Ishida1, Shohei Sugawara1, Shunya Honda1
1Department of Chemistry, Graduate School of Science, Tohoku University, Aoba-ku, Sendai 980-8578, Japan. ishida@tohoku.ac.jp takeaki.iwamoto@tohoku.ac.jp.
Abstract:
Naphthodislacyclobutadiene 3 and anthradisilacyclobutadiene 4 were synthesized and characterized. In these compounds, the diatropic ring current on the benzene ring adjacent to the disilacyclobutadiene moiety decreases while that on the other benzene rings remains intact. The longest-wavelength absorption bands of 3 and 4 were hypsochromically shifted compared to those of benzodisilacyclobutadiene 1a despite the extended π-electron systems.
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