- Azulene–Naphthalene-Type Rearrangements in Benz[a]azulene and Cyclohepta[b]indole
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Flash vacuum pyrolysis (FVP) of benz[a]azulene yields phenanthrene and 2-ethynylbiphenyl. FVP of cyclohepta[b]indole similarly yields phenanthridine and 2-cyanobiphenyl. The reversibility of the reactions is demonstrated by FVP of 2-ethynylbiphenyl and 2-isocyanobiphenyl. All the observed reactions are in accord with the norcaradiene–vinylidene mechanism of the azulene–naphthalene rearrangement, whereas other proposed mechanisms are ruled out.
- Wentrup, Curt,Becker, Jürgen
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p. 13835 - 13839
(2016/09/21)
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- THE REACTION OF 1,4-DIHYDROCYCLOPENTINDOLES WITH DIMETHYL ACETYLENEDICARBOXYLATE
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Diethyl 1,4-dihydro-4-methyl-3-(N-methyl-3-indolyl)cyclopentoindole-1,2-dicarboxylate (3) reacted with dimethyl acetylenedicarboxylate (DMAD) in acetonitrile under reflux to give the 5,10-dihydrocyclopentindole (5).The same reaction in benzene gave the maleate (or fumarate) (6) and the 1,1a,3a,4-tetrahydrocyclobutcyclopentindole (8).Thermolysis of 8 resulted in the formation of 5.In contrast to a cycloaddition reaction of 3 and DMAD, 2 reacted with two molecules of DMAD to give the 1,1a,5a,6-tetrahydrocyclohexcyclopentindole (10).Keywords: 1,4-dihydrocyclopentindole; dimethyl acetylenedicarboxylate; cycloaddition; 5,10-dihydrocyclopentindole; tetrahydrocyclobutcyclopentindole; tetrahydrocyclohexcyclopentindole.
- Kurihara, Takushi,Nasu, Keiko,Haginaga, Satomi
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p. 2456 - 2459
(2007/10/02)
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