ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Description / Table of Contents:
Heterodiamantanes and Structurally Related Compounds. Part II: The Pentacyclic C10-Diethers 5,12-Dioxapentacyclo [6.4.0.02,6.03,11.04,9]dodecane and 4,12-Dioxapentacyclo[6.3.1.02,7.03,10.05,9]dodecane
Notes:
No Abstract.In connection with studies on heterodiamantanes and structurally related compounds the two novel pentacyclic diethers 9 and 10 were prepared starting from the photo-dimer 8 of cyclopentadienone. All three compounds have as common features a central carbocyclic 6membered ring with four axial alkyl substituents and two oxygen function in 1,4-position. The diether 9 was obtained on the one hand from the intermediate tetracyclic unsaturated alcohol 23 by intramolecular addition, catalyzed either by acid or base (scheme 3), and on the other hand from the tetracyclic diol 32 or the dibromoketones 34 (via 38) and 35 (via 39) by intramolecular substitution (schemes 4 and 5). The synthesis of the isomeric diether 10 was achieved by intramolecular substitution of the tetracyclic diol 33 (scheme 4). Diether 9 is thermodynamically more stable than 10. The latter was easily isomerized to the former on treatment with concentrated sulfuric acid in benzene.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19800630730
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