ChemInform Abstract: CYCLOADDITIONS OF 3,4‐DIMETHOXYFURAN TO BENZOQUINONES

Hofmann, A.; Wyrsch‐Walraf, Ingeborg; Iten, Peter X.; Eugster, C. H.

doi:10.1002/chin.198008130

Chemischer Informationsdienst

1980

DOI: 10.1002/chin.198008130

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ChemInform Abstract: CYCLOADDITIONS OF 3,4‐DIMETHOXYFURAN TO BENZOQUINONES

A. Hofmann¹,

Ingeborg Wyrsch‐Walraf²,

Peter X. Iten³

et al.

Abstract: Cycloaddition der Titelverbindung (II) an die Benzochinone (Ia)‐(Ic) liefert die (isolierten) endo‐Addukte (IIIa) [nach Stehenlassen der Lösung ‐ Gemisch aus (IIIa) mit dem exo‐Isomeren (IVa)], (IIIb) bzw. (IIIc) [ nach längerem (90 h) Stehenlassen ‐+ 2 : 3‐(IIIc)/(IVb)‐ Gemisch]; mit dem Dimethylbenzochinon (Id) wird dagegen ausschließlich das exo‐ Addukt (IVc) gebildet.

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“…In contrast, the more active 3,4-dimethoxyfuran reacts smoothly with quinones under normal [2] or high-pressure conditions [ 11. These results stimulated us to reinvestigate the reaction between furan and nonactivated 1,4-benzoq~inones~).…”

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confidence: 99%

[2 + 4]‐Cycloaddition under High Pressure: First Realization of a Diels‐Alder Addition of Furan with Simple 1,4‐Benzoquinones. Preliminary Communication

Jurczak

Kozluk

Filipek

et al. 1983

Helvetica Chimica Acta

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SummaryFor the first time a successful [2+4]-cycloaddition of furan (1) with simple 1,4-benzoquinones 2 has been realized.Until now no report on a successful [2+ 41-cycloaddition of furan (1) with simple 1,4-benzoquinones 2 has been published. In contrast, the more active 3,4-dimethoxyfuran reacts smoothly with quinones under normal [2] or high-pressure conditions [ 11. These results stimulated us to reinvestigate the reaction between furan and nonactivated 1,4-benzoq~inones~). According to the literature [4] it could be expected that the Diels-Alder reaction would be accelerated by an increase of pressure, whereas the retro-reaction would be inhibited. Consequently we expected that under 20-22 kbar and at moderate temperatures (20-60") the equilibrium of the reaction is shifted to the side of products.High-pressure experiments on (1 : 1)-or (2 : 1)-mixtures of 1 and 2 were performed in ether solutions and in an apparatus of the piston-cylinder type3) with insertion of two or three Tejlon ampoules [6], thus permitting simultaneous realization of independent reactions in the same experiment. After reaction at 20 kbar and room temperature during 68 hours, the solvent was evaporated immediately upon decompression, and 'H-NMR. spectra were taken at -50". For results c$ the Scheme and Table 1. In each case beside the signals of starting materials new signals appeared which showed the characteristics of endo-and exo-cycloadducts 3 I ) 2, 3,Organic Syntheses under High Pressure, Part VI. For Part V see [ 11. For reactions of various furans with 'activated' 1.4-benzoquinones see 131; products of such reactions are always substituted furans. For the description see [S] [6].

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mentioning

confidence: 99%

[2 + 4]‐Cycloaddition under High Pressure: First Realization of a Diels‐Alder Addition of Furan with Simple 1,4‐Benzoquinones. Preliminary Communication

Jurczak

Kozluk

Filipek

et al. 1983

Helvetica Chimica Acta

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ChemInform Abstract: CYCLOADDITIONS OF 3,4‐DIMETHOXYFURAN TO BENZOQUINONES

Cited by 1 publication

References 1 publication

[2 + 4]‐Cycloaddition under High Pressure: First Realization of a Diels‐Alder Addition of Furan with Simple 1,4‐Benzoquinones. Preliminary Communication

[2 + 4]‐Cycloaddition under High Pressure: First Realization of a Diels‐Alder Addition of Furan with Simple 1,4‐Benzoquinones. Preliminary Communication

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