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Communication | Special issue | Vol 90, No. 1, 2015, pp.157-162
Published online, 16th July, 2014
DOI: 10.3987/COM-14-S(K)48
Tandem [4+2] Cycloaddition/Aromatization Sequence of Allenyl 2-Bromo-3-vinylcyclohex-2-enyl Thioether to Naphtho[1,8-bc]thiophene

Noriyuki Hatae,* Aiichirou Kaji, Chiaki Okada, and Eiko Toyota

*Faculty of Pharmaceutical Sciences, Health Sciences University of Hokkaido, Ishikari-Tobetsu, Hokkaido 061-0293, Japan


A concise synthetic route of tetrahydro-3H-naphtho[1,8-bc]thiophene was developed. Allenyl 2-bromo-3-vinylcyclohex-2-enyl thioether underwent a tandem [4+2] cycloaddition/aromatization sequence to produce the naphthothiophene with high yield. A density functional study for the transition and reaction enthalpies was performed to elucidate the details of the reaction.