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Strained Ketenes from α-Bromoacyl Phosphates. (Tricyclo[4.4.1.01,6]undeca-3,8-dien-11-ylidene)methanone and its Heptacyclic Dimer: a Dispirobridged Dipropellane (1,1″,4,4″,5,5″,8,8″-Octahydrodispiro[[4a, 8a]methanonaphthalene-9,1′-cyClobutane-3′,9″-[4a, 8a]methanonaphthalene]-2′, 4′-dione)

✍ Scribed by H. Martin R. Hoffmann; Peter M. Geschwinder; Hans-Peter Hollwege; Angela Walenta

Publisher
John Wiley and Sons
Year
1988
Tongue
German
Weight
454 KB
Volume
71
Category
Article
ISSN
0018-019X

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✦ Synopsis

Dehalogenation of the mixed anhydride 6 of 11-bromotricyclo[4.4.1 .0',6]undeca-3,8-diene-l 1-carboxylic acid (4) and of diethyl hydrogen phosphate with Zn-Ag couple in THF gave the dispiro-fused dipropellane 8 ( I , l", 4,4,5,5", 8,8"-octahydrodispiro[[4a, 8a]methanonaphthalene-9,1 '-cyclobutane-3',9-[4a,8a]methanonaph-thaIene]-2',4'-dione) in 58 % yield. Unlike other dispiro[2.1.2.l]octane-4,8-diones (see 2a-e), the new cyclodimer 8 is an 02-sensitive compound. The 1 1 -bromobicyclo[4.4. llundeca-I ,3,5,7,9-pentaene-1 1-carboxylic acid (1 3) 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.

Scheme I

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