Syntheses of new fulvene derivatives

UNCG Author/Contributor (non-UNCG co-authors, if there are any, appear on document)
James Cornette Burnette (Creator)
The University of North Carolina at Greensboro (UNCG )
Web Site:
David Knight

Abstract: Fulvenes, ylidenecyclopentadiene derivatives, bearing heteroatom substituents on the carbon atom alpha to C6 are unreported. This thesis reports the results of several attempts to construct fulvenes substituted in this manner. These new molecules are needed for continuing investigations into the effects on chemical reactivity of fulvene-type conjugation. Following generally applicable routes to fulvenes involving aldoltype condensation of cyclopentadienide salts and ketones, we have prepared fulvene derivatives of the type described above at the oxidation level of the alcohol, aldehyde, and ketone. After suitably blocking the hydroxyl group of pyruvic alcohol as the tetrahydropyranyl ether, treatment with cyclopentadienyl lithium gave the tetrahydropyranyl ether of 6-methyl-6-hydroxymethylfulvene (13) which upon acid hydrolysis was smoothly converted to the new compound, 6-methyl-6-hydroxymethylfulvene (11). This molecule fulfilled the criteria of a simple fulvene containing a heteroatom on carbon alpha to C6. The tetrahydropyranyl ether of 6-methyl-6-hydroxymethylfulvene was also prepared by treating pyruvyl-2-tetrahydropyranyl ether (12) and cyclopentadiene in the presence of cyclopentadienylcopper (I)- isocyanide.

Additional Information

Language: English
Date: 1973
Aldehydes $x Experiments
Ketones $x Experiments

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