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1,2,3,4,5‐Pentamethyl‐5‐acetyl‐cyclopentadien‐1,3, ein ungewöhnliches Keton
Author(s) -
Burger Ulrich,
Delay Arlette,
Mazenod François
Publication year - 1974
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.19740570725
Subject(s) - chemistry , cyclopentadiene , ketone , yield (engineering) , ethylene glycol , medicinal chemistry , diene , moiety , ethylene , stereochemistry , organic chemistry , catalysis , materials science , natural rubber , metallurgy
It has been shown that the reaction of the title ketone with phosphorous pentachloride leads to regiospecific chlorine transfer to the diene moiety of the molecule, leaving the carbonyl function intact. Attempted acetalization with ethylene glycol did not give the dioxolane but rather 1,2,3,4,5‐pentamethylcyclopenta‐1, 3‐diene in quantitative yield. An independent synthesis of this hydrocarbon, previously available only by lengthy multistep synthesis, has also been described. The only normal carbonyl reaction of the permethyl‐acetyl‐cyclopentadiene observed was the reduction by metal hydrides.