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Paper | Regular issue | Vol 45, No. 6, 1997, pp.1131-1142
Published online, 1st January, 1970
DOI: 10.3987/COM-97-7804
Cyclization of o-(3-Hydroxy-3-methylbutynyl)phenols with Boron Tribromide to 4-Bromo-2,2-dimethylchromenes and Their Electroreduction to 2,2-Dimethylchromenes

Masao Tsukayama,* Hideyuki Utsumi, Akira Kunugi, and Hiroshi Nozaki

*Department of Chemical Science and Technology, Faculty of Engineering, University of Tokushima, Minamijosanjima-cho, Tokushima 770-0814, Japan


Cyclization of o-(3-hydroxy-3-methylbutynyl)phenols (2) with boron tribromide gave easily 4-bromo-2,2-dimethylchromenes (3). Electrolytic reduction of 3 at a Hg-pool electrode afforded the corresponding 2,2-dimethylchromenes (6) in high yields.