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1 article(s) from Blencowe, Anton

An overview of the cycloaddition chemistry of fulvenes and emerging applications

Ellen Swan,
Kirsten Platts and
Anton Blencowe

Beilstein J. Org. Chem. 2019, 15, 2113–2132, doi:10.3762/bjoc.15.209

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Graphical Abstract

Figure 1: General structure of fulvenes, named according to the number of carbon atoms in their ring. Whilst ...

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Figure 2: Generic structures of commonly referenced heteropentafulvenes, named according to the heteroatom su...

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Scheme 1: Resonance structures of (a) pentafulvene and (b) heptafulvene showing neutral (1 and 2), dipolar (1a...

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Scheme 2: Resonance structures of (a) pentafulvenes and (b) heptafulvenes showing the influence of EDG and EW...

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Scheme 3: Reaction of 6,6-dimethylpentafulvene with singlet state oxygen to form an enol lactone via the mult...

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Scheme 4: Photosensitized oxygenation of 8-cyanoheptafulvene with singlet state oxygen to afford 1,4-epidioxi...

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Figure 3: A representation of HOMO–LUMO orbitals of pentafulvene and the influence of EWG and EDG substituent...

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Scheme 5: Reactions of (a) 6,6-dimethylpentafulvene participating as 2π and 4π components in cycloadditions w...

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Scheme 6: Proposed mechanism for the [6 + 4] cycloaddition of tropone with dimethylfulvene via an ambimodal [...

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Scheme 7: Triafulvene dimerization through the proposed 'head-to-tail' mechanism. The dipolar transition stat...

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Scheme 8: Dimerization of pentafulvenes via a Diels–Alder cycloaddition pathway whereby one fulvene acts as a...

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Scheme 9: Dimerization of pentafulvenes via frustrated Lewis pair chemistry as reported by Mömming et al. [116].

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Scheme 10: Simplified reaction scheme for the formation of kempane from an extended-chain pentafulvene [127].

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Scheme 11: The enantioselective (>99% ee), asymmetric, catalytic, intramolecular [6 + 2] cycloaddition of fulv...

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Scheme 12: Intramolecular [8 + 6] cycloaddition of the heptafulvene-pentafulvene derivative [22,27].

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Scheme 13: Reaction scheme for (a) [2 + 2] cycloaddition of 1,2-diphenylmethylenecyclopropene and 1-diethylami...

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Scheme 14: Diels–Alder cycloaddition of pentafulvenes derivatives participating as dienes with (i) maleimide d...

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Scheme 15: Generic schemes showing pentafulvenes participating as dienophiles in Diels–Alder cycloadditions wi...

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Scheme 16: Reaction of 8,8-dicyanoheptafulvene and styrene derivatives to afford [8 + 2] and [4 + 2] cycloaddu...

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Scheme 17: Reaction of 6-aminofulvene and maleic anhydride, showing observed [6 + 2] cycloaddition; the [4 + 2...

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Scheme 18: Schemes for Diels–Alder cycloadditions in dynamic combinatorial chemistry reported by Boul et al. R...

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Scheme 19: Polymerisation and dynamer formation via Diels–Alder cycloaddition between fulvene groups in polyet...

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Scheme 20: Preparation of hydrogels via Diels–Alder cycloaddition with fulvene-conjugated dextran and dichloro...

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Scheme 21: Ring-opening metathesis polymerisation of norbornene derivatives derived from fulvenes and maleimid...

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Review

Published 06 Sep 2019

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