ISSN:
0018-019X
Schlagwort(e):
Chemistry
;
Organic Chemistry
Quelle:
Wiley InterScience Backfile Collection 1832-2000
Thema:
Chemie und Pharmazie
Notizen:
Dehalogenation of the mixed anhydride 6 of 11-bromotricyclo[4.4.1.01,6] undeca-3,8-diene-11-carboxylic acid (4) and of diethyl hydrogen phosphate with Zn-Ag couple in THF gave the dispiro-fused dipropellane 8(1,1″,4,4″,5,5″,8,8″-octahydrodispiro[[4a, 8a]methanonaphthalene-9,1′-cyclobutane-3′,9″-[4a, 8a]methanonaphthalene]-2′,4′-dione) in 58% yield. Unlike other dispiro[2.1.2.1]octane-4, 8-diones (see 2a-e), the new cyclodimer 8 is an O2-sensitive compound. The 11-bromobicyclo[4.4.1] undeca-1,3,5,7,9-pentaene-11-carboxylic acid (13) was prepared and converted into the acyl phosphate 14, which in turn was reduced with Zn-Ag couple in THF/MeOD to give the deuterated ester 16. Other cyclopropylidenemethanones could be generated and dimerized advantageously by the Zn-induced reduction of the mixed anhydride of the 1-bromocyclopropanecarboxylic acid and diethyl hydrogen phosphonate.
Materialart:
Digitale Medien
URL:
http://dx.doi.org/10.1002/hlca.19880710812
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