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Communication | Regular issue | Vol 19, No. 7, 1982, pp.1197-1202
Published online, 1st January, 1970
DOI: 10.3987/R-1982-07-1197
■ Cycloaddition Reactions of 1-Ethoxycarbonyl-1H-azepine and 1-Ethoxycarbonyl-1H-1,2-diazepine with 3,4,5,6-Tetrachloro-1,2-benzoquinone

Katsuhiro Saito, Shigenori Iida, and Toshio Mukai

*Faculty of Engineering, Nagoya Institute of Technology, Gokiso-cho, Showa-ku, Nagoya 466-8555, Japan

Abstract

The reaction of 1-ethoxycarbonyl-1H-azepine (1) with 3,4,5,6-tetrachloro-1,2-benzoquinone at room temperature afforded a [6+4] type cycloadduct 3 as a major product in addition to two [4+2] type cycloadducts 4 and 5. Upon heating, 3 rearranged to 5 in a fairly good yield. In the same reaction with 1-ethoxycarbonyl-1H-1,2-diazepine (2), a [4+2] type cycloadduct 6 was formed. The low electron density at the 2 and 7 positions of 1 is considered to be one reason for the formation of the [6+4] type cycloadduct 3.