1522-2675/asset/cover.gif?v=1&s=e7759ff8d29b48c9d72e374a3514f2b3582e876e "Helvetica Chimica Acta")
Universität Zürich.
1522-2675/asset/olbannerleft.gif?v=1&s=0a889c60e0ef40903d4ba13bd831c5e15b98dbed)
1522-2675/asset/olbannerright.gif?v=1&s=509a5e625099b16b78168cbfd0b39bb155798884)
Article
Hexamethyl-2-oxabicyclo [3.2.0] hepta-3,6-dien†
Article first published online: 25 OCT 2004
DOI: 10.1002/hlca.19710540610
Copyright © 1971 Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Baumann, B. C., Rey, M., Markert, J., Prinzbach, H. and Dreiding, A. S. (1971), Hexamethyl-2-oxabicyclo [3.2.0] hepta-3,6-dien. HCA, 54: 1589–1599. doi: 10.1002/hlca.19710540610
- †
Aus der Diplomarbeit von B. C. Baumann, Universität Zürich, 1971.
- ‡
Universität Zürich.
- §
Stipendiat des Fonds zur Unterstützung von Doktoranden auf dem Gebiete der Chemie.
- ¶
Universität Freiburg.
Publication History
- Issue published online: 25 OCT 2004
- Article first published online: 25 OCT 2004
- Abstract
- References
- Cited By
Abstract
Substance X, one of the three compounds obtained upon heating 5, 6-endo-epoxy-hexamethyl-bicyclo[2.2.0]hex-2-ene (11) and previously postulated by Klaus et al. [10] to be 5-acetyl-pentamethyl-bicyclo[2.1.0]pentene (9), is now shown to be hexamethyl-2-oxabicyclo[3.2.0]-hepta-3, 6-diene (10) by reinterpretation and supplementation of the spectral data and by ozonization of the dihydro derivative 16, which yields 1-acetoxy-2-acety-1-1, 2, 3, 4-tetramethyl-cyclo-butane (17). It is concluded that the Claisen equilibrium in this system lies entirely on the side of the enol ether 10; even drastic LiAIH4 conditions cannot force a reversal (10 → 9). Tetracyanoethylene adds to the enolic double bond of 10 to form the cyclo-adduct 19.