ISSN:
0009-2940
Keywords:
Oxepines
;
Furans
;
Ruthenium tetroxide
;
Iron complexes
;
Heterophanes
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Synthesis of Medium and Large Rings, XXXI[1] - The [6](3,6)Oxepinophane-[6](2,5)Furanophane Ring Contraction with Ruthenium TetroxideA one-pot synthesis of the furanophanes 2a and 2b by ring contraction of the oxepinophanes 1a and 1b is described. Evidence is presented that the reaction proceeds by subsequent oxidation of two double bonds via the intermediates 3 and 4. On treatment with hydrochloric acid cis-4 gives 2a by 1,4-elimination of hydrogen peroxide. The oxidation of the [7](3,6)oxepinophane 1c leads to a complex mixture of the products 2d and 6-10. 2a undergoes Diels-Alder reactions with benzyne and 2,3-naphthalyne to give 11 and 12. The latter forms the stable iron tricarbonyl complex 13. The structures of 2c, 4, 10, 11, and 13 have been established by X-ray analyses.
Additional Material:
5 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19921250626
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