Reactivity of long conjugated systems: Selectivity of Diels-Alder cycloaddition in oligofurans

Ori Gidron; Linda J.W. Shimon; Gregory Leitus; Michael Bendikov

doi:10.1021/ol202987e

Reactivity of long conjugated systems: Selectivity of Diels-Alder cycloaddition in oligofurans

Ori Gidron, Linda J.W. Shimon, Gregory Leitus, Michael Bendikov^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

37 Scopus citations

Abstract

Taking advantage of the synthetic availability and solubility of long oligofurans, their reactivity toward dienophiles was studied as a model for the rarely investigated reactivity of long conjugated systems. Unlike oligoacenes, the reactivity of oligofurans decreases or remains constant with increasing chain length. Terminal ring cycloadducts of oligofurans are kinetically and thermodynamically favored, whereas central ring cycloadducts are preferred in oligoacenes, because of the different driving forces in the two reactions: π-conjugation in oligofurans and aromatization/dearomatization in oligoacenes.

Original language	English
Pages (from-to)	502-505
Number of pages	4
Journal	Organic Letters
Volume	14
Issue number	2
DOIs	https://doi.org/10.1021/ol202987e
State	Published - 20 Jan 2012
Externally published	Yes

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abstract = "Taking advantage of the synthetic availability and solubility of long oligofurans, their reactivity toward dienophiles was studied as a model for the rarely investigated reactivity of long conjugated systems. Unlike oligoacenes, the reactivity of oligofurans decreases or remains constant with increasing chain length. Terminal ring cycloadducts of oligofurans are kinetically and thermodynamically favored, whereas central ring cycloadducts are preferred in oligoacenes, because of the different driving forces in the two reactions: π-conjugation in oligofurans and aromatization/dearomatization in oligoacenes.",

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T2 - Selectivity of Diels-Alder cycloaddition in oligofurans

AU - Gidron, Ori

AU - Shimon, Linda J.W.

AU - Leitus, Gregory

AU - Bendikov, Michael

PY - 2012/1/20

Y1 - 2012/1/20

N2 - Taking advantage of the synthetic availability and solubility of long oligofurans, their reactivity toward dienophiles was studied as a model for the rarely investigated reactivity of long conjugated systems. Unlike oligoacenes, the reactivity of oligofurans decreases or remains constant with increasing chain length. Terminal ring cycloadducts of oligofurans are kinetically and thermodynamically favored, whereas central ring cycloadducts are preferred in oligoacenes, because of the different driving forces in the two reactions: π-conjugation in oligofurans and aromatization/dearomatization in oligoacenes.

AB - Taking advantage of the synthetic availability and solubility of long oligofurans, their reactivity toward dienophiles was studied as a model for the rarely investigated reactivity of long conjugated systems. Unlike oligoacenes, the reactivity of oligofurans decreases or remains constant with increasing chain length. Terminal ring cycloadducts of oligofurans are kinetically and thermodynamically favored, whereas central ring cycloadducts are preferred in oligoacenes, because of the different driving forces in the two reactions: π-conjugation in oligofurans and aromatization/dearomatization in oligoacenes.

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Reactivity of long conjugated systems: Selectivity of Diels-Alder cycloaddition in oligofurans

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