| Title | Studies in the cycloproparene series: Oxygen-containing 1H-cyclopropa[b]naphthalenes and their methylidene derivatives |
| Publication Type | Journal Article |
| Year of Publication | 1996 |
| Authors | Halton, B., Kay A.J., Zhi-mei Z., Boese R., and Haumann T. |
| Journal | Journal of the Chemical Society - Perkin Transactions 1 |
| Issue | 12 |
| Pagination | 1445 - 1452 |
| Date Published | 1996 |
| ISSN | 0300922X (ISSN) |
| Abstract | 3,6-Dimethoxy-1H-cyclopropa[b]naphthalene 4 is available from 1,4-benzoquinone in four steps in 27-28% overall yield. The diether 4 provides a range of methylidene derivatives 15a-e by way of the disilyl compound 14, and is efficiently demethylated by cerium(IV) ammonium nitrate to provide 1H-cyclopropa[b]naphthalene-3,6-dione 16 (85%) whose crystal structure is reported. Quinone 16 is the first stable cyclopropaquinone but it resists conversion into a 1-C exocyclic olefin. The chemistry of the compounds is described, their spectral data are discussed, and the cyclic voltammetry of 16 is provided. |
| URL | http://www.scopus.com/inward/record.url?eid=2-s2.0-33748908382&partnerID=40&md5=0aa7e13b1c8f00180f13b2ba0b8f3af8 |
