82697-83-4Relevant academic research and scientific papers
and Type Cycloaddition Reactions of 1-Ethoxycarbonyl-1H-azepine and 1-Ethoxycarbonyl-1H-1,2-diazepine with 3,4,5,6-Tetrachloro-1,2-benzoquinone
Saito, Katsuhiro,Mukai, Toshio,Iida, Shigenori
, p. 2485 - 2488 (1986)
The reaction of 1-ethoxycarbonyl-1H-azepine with 3,4,5,6-tetrachloro-1,2-benzoquinone at room temperature gave a -type cycloadduct as the major product and two kinds of -type cycloadducts.In this reaction the diketone moiety of the benzoquinone derivative was used as the 4? component to form ether linkages.The -type cycloadduct became rearranged to one of the -type cycloadducts by heating at 90 deg C.The same reaction, but using 1-ethoxycarbonyl-1H-1,2-diazepine, afforded two kinds of -type cycloadducts.An electronic attraction between the oxygen atoms of the benzoquinone derivative and the carbons in the 2 and 7-positions of the azepine derivative is considered to be one of the driving force of the -type cycloaddition reaction.The -type cycloadducts are regarded to be formed via inverse electron demand Diels-Alder reactions.
CYCLOADDITION REACTIONS Of 1-ETHOXYCARBONYL-1H-AZEPINE AND 1-ETHOXYCARBONYL-1H-1,2-DIAZEPINE WITH 3,4,5,6-TETRACHLORO-1,2-BENZOQUINONE
Saito, Katsuhiro,Iida, Shigenori,Mukai, Toshio
, p. 1197 - 1202 (2007/10/02)
The reaction of 1-ethoxycarbonyl-1H-azepine (1) with 3,4,5,6-tetrachloro-1,2-benzoquinone at room temperature afforded a type cycloadduct 3 as a major product in addition to two 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 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 type cycloadduct 3.
