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Paper | Regular issue | Vol 71, No. 11, 2007, pp.2465-2476
Published online, 3rd August, 2007
DOI: 10.3987/COM-07-11153
Synthesis and Redox Ring Cleavage of cis-1,3,4,5-Tetrahydrobenzo[c]oxepines

Xinfang Duan, Xiali Xu, Zhanbin Zhang,* and Zhibing Zheng

*Department of Chemistry, Beijing Normal University, Beijing, 100875, China

Abstract

A series of cis-1,3,4,5-tetrahydrobenzo[c]oxepines was conveniently prepared via the oxa-Pictet-Spengler reaction catalyzed by boron trifluoride etherate in dioxane at room temperature. Experiments proved that the construction of these heterocyclic compounds via this methodology was highly acid (catalyst)- and reaction condition-dependent. An unexpected redox ring cleavage reaction occurred when unsuitable acids or reaction conditions were employed.