Electrophilic Substitution Reactions of [1]Benzothieno[3,2-<i>b</i>]furan

Svoboda, Jiří; Pihera, Pavel; Sedmera, Petr; Paleček, Jaroslav

doi:10.1135/cccc19960888

CCCC > Archive > 1996, Volume 61 > Issue 6 > p. 888

Electrophilic Substitution Reactions of [1]Benzothieno[3,2-b]furan

Jiří Svoboda^a, Pavel Pihera^a, Petr Sedmera^b and Jaroslav Paleček^a

^a Institute of Organic Chemistry, Prague Institute of Chemical Technology, 166 28 Prague 6, Czech Republic
^b Institute of Microbiology, Academy of Sciences of the Czech Republic, 142 20 Prague 4, Czech Republic

Abstract

In chlorination, bromination, iodination, nitration, sulfonation, formylation, and trifluoroacetylation of [1]benzothieno[3,2-b]furan (1) the substituent enters the 2-position. The said halogenations go by the addition-elimination mechanism. When the substitution is continued, the second substituent enters the 6-position of heterocycle 1. The ¹H and ¹³C NMR spectra have been completely assigned. Substituent effects on NMR parameters are discussed.

Keywords: [1]Benzothieno[3,2-b]furan; Electrophilic substitution.

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Electrophilic Substitution Reactions of [1]Benzothieno[3,2-b]furan

Abstract