Reactivity of indanedioneketene dimer with amines.
The highly reactive indanedioneketene 5, resulting from the thermal decomposition of phenyliodonium ylide of 2-hydroxy-1,4-naphthoquinone (lawsone, 4), in the absence of nucleophiles dimerizes to the corresponding tetraoxo spiro oxetanone 6 in quantitative yield. This oxetanone exhibits an interesting reactivity toward amines.
Malamidou-Xenikaki
Elizabeth
E
Department of Chemistry, Aristotle University of Thessaloniki, 54124 Thessaloniki, Greece. malamido@chem.auth.gr
Spyroudis
Spyros
S
Tsanakopoulou
Maria
M
Krautscheid
Harald
H
D000588:Amines / Q000737:chemistry*; D018360:Crystallography, X-Ray; D019281:Dimerization; D006860:Hydrogen Bonding; D007189:Indans / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D009285:Naphthoquinones / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism; D013696:Temperature
D000588:Amines; D007189:Indans; D007659:Ketones; D009285:Naphthoquinones; C518112:indanedioneketene; C005090:lawsone