Furanodendralenes

Fallon, Thomas; Willis, Anthony C.; Paddon‐Row, Michael N.; Sherburn, Michael S.

doi:10.1021/jo500458y

Cited by 16 publications

(8 citation statements)

References 22 publications

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“…Paddon-Row and co-workers have reported a tandem DA reactions of furan-based dendralenes with the maleimide under microwave irradiation conditions . To this end, the furanodendralenes, 3,4-divinylfuran 275 was synthesized from 3,4-dibromofuran and vinyl magnesium bromide by the nickel-catalyzed Kumada–Tamao–Corriu cross-coupling reaction.…”

Section: Dendralenementioning

confidence: 99%

Diversity-Oriented Approaches to Polycyclics and Bioinspired Molecules via the Diels–Alder Strategy: Green Chemistry, Synthetic Economy, and Beyond

2015

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We describe diverse approaches to various dienes and their utilization in the Diels-Alder reaction to produce a variety of polycycles. The dienes covered here are prepared by simple alkylation reaction or via the Claisen rearrangement or by enyne metathesis of alkyne or enyne building blocks. Here, we have also included the Diels-Alder chemistry of dendralenes, a higher analog of cross-conjugated dienes. The present article is inclusive of o-xylylene derivatives that are generated in situ starting with benzosultine or benzosulfone derivatives. The Diels-Alder reaction of these dienes with various dienophiles gave diverse polycyclic systems and biologically important targets.

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Section: Dendralenementioning

confidence: 99%

Diversity-Oriented Approaches to Polycyclics and Bioinspired Molecules via the Diels–Alder Strategy: Green Chemistry, Synthetic Economy, and Beyond

2015

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“…165 The most recent investigation of this transformation was published by Paddon-Row and Sherburn in 2009. 166 The reaction of bicyclic dienyne 181 with fumaronitrile to form D-homosteroid structures 183 and 184 is representative (Scheme 41). Two consecutive dehydro-DA reactions gave the tetracyclic double DA adducts by way of putative intermediate 182, in a reaction best performed under microwave heating.…”

Section: Review Syn Thesismentioning

confidence: 99%

The Diels–Alder Reaction in Steroid Synthesis

Mackay

Sherburn

2014

Synthesis

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This review explores the myriad ways in which the Diels-Alder reaction has been employed in the construction of the tetracyclic steroid nucleus. A systematic analysis of possible approaches highlights both the synthetic versatility of this ubiquitous reaction and also opportunities for new routes to fused tetracarbocyclic steroid frameworks. 1.1 Introduction 1.2 Classification of the Approaches 2.1 Installation of a Non-Skeletal Ring 2.2 Construction of the A-Ring 2.3 Construction of the BRing 2.4 Construction of the C-Ring 2.5 Double Diels-Alder Sequences 3 Conclusions and Future Prospects

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“…Furan based π-conjugated materials have been attained more interests during the past decade, because furan containing OSMs are more stable and potentially applicable in modern era optoelectronic devices like organic field effect transistor (OFETs), organic solar cells, organic light emitting transistor (OLETs), and organic light-emitting diodes (OLEDs) [18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35].…”

Section: Introductionmentioning

confidence: 99%

Effect of donor strength of extended alkyl auxiliary groups on optoelectronic and charge transport properties of novel naphtha[2,1-b:6,5-b′]difuran derivatives: simple yet effective strategy

et al. 2015

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The present study spotlights the designing of new derivatives of 2,7-bis (4-octylphenyl) naphtho [2,1-b:6,5-b'] difuran (C8-DPNDF) by substituting the alkyl groups (methyl, ethyl, propyl, butyl, pentyl, hexyl, and heptyl groups) at para position. Density functional theory (DFT) and time-dependent density functional theory (TD-DFT) methods are employed to optimize the molecular structures in ground and first excited states, respectively. Several electro-optical properties including hole/electron reorganization energies (λh/λe), electron affinities (EAs), ionization potentials (IPs), molecular electrostatic potentials (MEP), and frontier molecular orbitals (FMOs) have been evaluated. Furthermore their transfer integrals and intrinsic mobilities values have also been calculated. From this study, it is found that hole mobility of octyl containing derivative is raised to 4.69 cm(2) V(-1) s(-1). Moreover with attaching octyl group, hole transfer integral values have also been enhanced in newly designed derivatives. The balanced hole and electron reorganization energies, and improved transfer integrals lead to enhanced mobility in derivatives with octyl group, highlighting them as an efficient hole transfer material. Unlike the other electro-optical properties, the intrinsic hole mobility has increased because of transfer integral values of octyl containing derivative C8-DPNDF due to the dense and close crystal packing of C8-DPNDF. However, photostability of furan-based materials has not changed by increasing length of extended alkyl chain. Thus our present investigation highlights the importance of alkyl auxiliary groups that are often neglected/replaced with simple methyl group to save computation costs. Graphical Abstract The hole and electron reorganization energies of naphtho[2,1-b:6,5-b']difuran derivatives.

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Furanodendralenes

Abstract: An examination of Diels-Alder reactions of furan-containing analogues of dendralenes has revealed complex and fascinating reaction sequences, which chart the inherent site and stereoselectivity of these processes and give rapid access to structures of high molecular complexity.

Cited by 16 publications

References 22 publications

Diversity-Oriented Approaches to Polycyclics and Bioinspired Molecules via the Diels–Alder Strategy: Green Chemistry, Synthetic Economy, and Beyond

Diversity-Oriented Approaches to Polycyclics and Bioinspired Molecules via the Diels–Alder Strategy: Green Chemistry, Synthetic Economy, and Beyond

The Diels–Alder Reaction in Steroid Synthesis

Effect of donor strength of extended alkyl auxiliary groups on optoelectronic and charge transport properties of novel naphtha[2,1-b:6,5-b′]difuran derivatives: simple yet effective strategy

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