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ChemInform Abstract: A Novel Isomerization of 6,6-Tetramethylenefulvene to Cyclopent-1-enyl Cyclopentadiene and Its Cycloaddition Reactions: Synthesis of Polycyclic Molecular Frameworks.

✍ Scribed by V. NAIR; J. S. NAIR; S. KUMAR; N. P. RATH; P. G. WILLIARD; G. K. EIGENDORF

Publisher: John Wiley and Sons
Year: 2010
Weight: 33 KB
Volume: 29
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199837085

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✦ Synopsis

Tetramethylenefulvene to Cyclopent-1enyl Cyclopentadiene and Its Cycloaddition Reactions: Synthesis of Polycyclic Molecular Frameworks.

-6,6-Tetramethylenefulvene (III), obtained in solution by base-mediated condensation of cyclopentadiene with cyclopentanone, undergoes acid-mediated rearrangement to the triene (IV). This reacts with reactive dienes such as (V) to give the [4 + 2] cycloadduct (VI) together with the dimer. Less reactive dienes [cf. (VII)] provide rapid dimerization and subsequent Diels-Alder reaction.

-(NAIR, V.; NAIR,

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