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Addition von Dimethylketen an 6‐heterosubstituierte Fulvene. Synthese von (±)‐Filifolon
Author(s) -
Stadler Heinz,
Rey Max,
Dreiding André S.
Publication year - 1984
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19840670722
Subject(s) - fulvene , chemistry , cycloaddition , fulvenes , adduct , diketone , medicinal chemistry , raney nickel , yield (engineering) , stereochemistry , organic chemistry , catalysis , materials science , metallurgy
Addition of Dimethylketene to 6‐Heterosubstituted Fulvenes. Synthesis of (±)‐Filifolone [2 + 2]Cycloaddition of dimethylketene to 6‐ethoxy‐ ( 8 ) and 6,6‐(tetramethylenedithio)fulvene ( 9 ) gave the 4‐alkylidenebicyclo[3.2.0]heptenones 11 and 12 , respectively. Under the same conditions, 6‐(dimethylamino)fulvene ( 7 ) was acylated to yield the push‐pull fulvene 10 . Raney ‐Ni reduction converted the adduct 12 into the monoterpene (±)‐filifolone ((±)‐ 1 , 52%) and minor amounts of the four related ketones 14 ‐ 17 . Cycloaddition of a second dimethylketene to the primary cycloadduct 11a yielded the cis, transoid, cis ‐tricyclic diketone 13 .