Unique formation of oxapentacycloundecanones by catalytic flash vacuum thermolysis of tricyclo[5.2.1.02,6]decenone epoxides using mineral solid acids

Author:

Derksen André J.,van der Waals Adri C.L.M.,van Ham Marieke H.A.,van Dongen Mark,Borkent Jan H.,de Gelder René,Klunder Antonius J.H.,Zwanenburg Binne

Publisher

Elsevier BV

Subject

Organic Chemistry,Drug Discovery,Biochemistry

Reference16 articles.

1. (a) Van der Waals, A. C. L. M.; Klunder, A. J. H.; Van Buren, F. R.; Zwanenburg, B. J. Mol. Catal. A. 1998, 134, 179–189.

2. (b) Klunder, A. J. H.; Van der Waals, A. C. L. M.; Zwanenburg, B. In Supported Reagents and Catalysts in Chemistry, Hodnett, B. K.; Kybett, A. P.; Clark, J. H.; Smith, K., Eds.; The Royal Society of Chemistry: Cambridge, 1998, pp. 13–18.

3. (a) Klunder, A. J. H.; Bos, W.; Verlaak, J. M. J.; Zwanenburg, B. Tetrahedron Lett. 1981, 22, 4553–4556.

4. (b) Verlaak, J. M. J.; Klunder, A. J. H.; Zwanenburg, B. Tetrahedron Lett. 1982, 23, 5463–5466.

5. Amorphous alumina B698D-24 and the acid-treated natural clay Grade F-1 were received as generous gifts from Engelhard De Meern B.V., The Netherlands. The catalysts used, were pressed (3 tons) and sieved to the desired particle size (150–425 μm). Catalysts were used after a pre-treatment: an amount of catalyst was placed on a quartz porous filter in the middle of a quartz FVT-tube. Using the catalytic FVT set-up, the catalyst was equilibrated at a temperature of 400°C and a vacuum of 0.05 mbar during 15–20 min to remove physisorbed water.

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