Photo-induced β-elimination of 9-fluorenylmethanol leading to dibenzofulvene

Hassan Nageh; Liming Zhao; Akira Nakayama; Jun-Ya Hasegawa; Yue Wang; Tamaki Nakano

doi:10.1039/c7cc03297h

Photo-induced β-elimination of 9-fluorenylmethanol leading to dibenzofulvene

Chem Commun (Camb). 2017 Jul 25;53(60):8431-8434. doi: 10.1039/c7cc03297h.

Authors

Hassan Nageh¹, Liming Zhao¹, Akira Nakayama¹, Jun-Ya Hasegawa², Yue Wang¹, Tamaki Nakano²

Affiliations

¹ Institute for Catalysis (ICAT) and Graduate School of Chemical Sciences and Engineering, Hokkaido University, N 21, W 10, Kita-ku, Sapporo 001-0021, Japan. tamaki.nakano@cat.hokudai.ac.jp.
² Institute for Catalysis (ICAT) and Graduate School of Chemical Sciences and Engineering, Hokkaido University, N 21, W 10, Kita-ku, Sapporo 001-0021, Japan. tamaki.nakano@cat.hokudai.ac.jp and Integrated Research Consortium on Chemical Sciences (IRCCS), Institute for Catalysis, Hokkaido University, N21W10, Kita-ku, Sapporo 001-0021, Japan.

PMID: 28702520
DOI: 10.1039/c7cc03297h

Abstract

An effective photo-induced β-elimination of an alcohol leading to a vinyl compound is introduced for the first time. 9-Fluorenylmethanol was irradiated in a solution using a Xe lamp and was efficiently converted to dibenzofulvene (DBF) (9-methylenefluorene) in the absence of base which is necessary in the corresponding ground-state reaction.