| Title | Studies in the cycloproparene series: Chemistry of 1H-cyclopropa[b]naphthalene-3,6-dione and its transformation into lH-cyclopropa[b]anthracene-3,8-dione |
| Publication Type | Journal Article |
| Year of Publication | 2000 |
| Authors | Halton, B., Jones C.S., Kay A.J., Margetic D., and Sretenovic S. |
| Journal | Journal of the Chemical Society, Perkin Transactions 1 |
| Issue | 14 |
| Pagination | 2205 - 2210 |
| Date Published | 2000 |
| ISSN | 14704358 (ISSN) |
| Keywords | Addition reactions, Bromine, Chemical bonds, Dehydrogenation, Enolisation, Naphthalene, stoichiometry |
| Abstract | 1H-Cyclopropa[b]naphthalene-3,6-dione 3 adds bromine stoichiometrically across the enedione C=C bond to give dibromodihydrocyclopropanaphthalenedione 10 while with an excess of the reagent (bromomethyl)tribromonaphthoquinone 12 is formed. Typical quinone character is exhibited by 3 in Diels-Alder cycloadditions and it gives the endo-methanocyclopropanthraquinone 14 with cyclopentadiene. With buta-1,3-diene the analogous tetrahydrocyclopropanthraquinone 15 is formed from a temperature dependent reaction. Above 45°C opening of the three-membered ring of 4 also occurs and the cyclopentanthracenedione 16 is obtained from [π2 + π4] and [σ2 + π2] additions; it is the sole product at 100°C. Enolisation of the tetrahydroanthraquinone 15 provides diphenolate 18 and this can be diverted to diether 19 or readily oxidized to the dihydroanthraquinone 20. In turn, 20 is dehydrogenated to the fully aromatic cyclopropa[b]anthracene-3,8-dione 4, the first anthraquinone of the cycloproparene series. © The Royal Society of Chemistry 2000. |
| URL | http://www.scopus.com/inward/record.url?eid=2-s2.0-0034698436&partnerID=40&md5=91f3650a0111376ebca9440f249982be |
| DOI | 10.1039/b002683m |
