Transformation of azulenes to bicyclic [4]dendralene and heptafulvene derivatives via photochemical cycloaddition of dialkylsilylene

Tomoyuki Kosai; Shintaro Ishida; Takeaki Iwamoto

doi:10.1039/c5cc03424h

Transformation of azulenes to bicyclic [4]dendralene and heptafulvene derivatives via photochemical cycloaddition of dialkylsilylene

Chem Commun (Camb). 2015 Jul 7;51(53):10707-9. doi: 10.1039/c5cc03424h.

Authors

Tomoyuki Kosai¹, Shintaro Ishida, Takeaki Iwamoto

Affiliation

¹ Department of Chemistry, Graduate School of Science, Tohoku University, Aoba-ku, Sendai 980-8578, Japan. sishida@m.tohoku.ac.jp iwamoto@m.tohku.ac.jp.

PMID: 26050797
DOI: 10.1039/c5cc03424h

Abstract

Regioselective cycloaddition of dialkylsilylene upon irradiation at 440 nm converts azulene and guaiazulene to bicyclic [4]dendralene and heptafulvene derivatives, respectively. Significant σ-π interactions in the resulting new silacycles were suggested using UV-vis spectra and theoretical calculations.