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Paper | Special issue | Vol 76, No. 1, 2008, pp.667-678
Published online, 1st May, 2008
DOI: 10.3987/COM-08-S(N)60
Preparation of 1,3,3a,7a-Tetrahydroisothianaphthene and Its Application to Tetrahydrothiophene-Fused Porphyrin

Yukiko Katsuyama, Eita Yoshida, Hiroki Uoyama, Noboru Ono, and Hidemitsu Uno*

*Division of Synthesis and Analysis, Department of Molecular Science, Integrated Center for Sciences, Ehime University, Matsuyama 790-8577, Japan

Abstract

Dehydrobromination of 5,6-dibromoperhydroisothianaphthene with DBU gave a mixture of 1,3,3a,7a-tetrahydroisothianaphthene and 1,3,3a,4-tetrahydroisothianaphthene in a ratio of 5:1. The former compound acted as an s-cis diene in the Diels-Alder reaction with bis(phenylsulfonyl)ethylene to give an adduct, which was successively converted to tetrahydrothiphene-fused pyrroles and porphyrins.