Synthesis and photochemistry of 2‐styrylpyrroles. Intermolecular photoaddition of pyrroles to a double bond

Šindler‐Kulyk, Marija; Tomšić, Slavica; Marinić, Željko; Metelko, Biserka

doi:10.1002/recl.19951141109

Cited by 28 publications

(18 citation statements)

References 20 publications

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“…Analogous electrocyclization was not detected in the phenylor furyl-substituted o-divinylbenzenes that have been studied to date. In the case of the phenyl-or furyl-substituted o-divinylbenzenes, stilbene-like 6π electrocyclization and formation of 1-vinylphenanthrene [32] or 6-vinylnaphtho[2,1-b]thiophene [30] was seen, respectively.…”

Section: Resultsmentioning

confidence: 99%

Versatile Photochemical Reactivity of Diverse Substituted 2‐, 4‐ and 5‐(o‐Vinylstyryl)oxazoles

et al. 2018

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To study the effects of the position of the hexatrienyl moiety on the oxazole ring, novel substituted cis/trans‐2/4/5‐(2‐vinylstyryl)oxazoles have been synthesized. These novel compounds were prepared by Wittig reaction from the diphosphonium salt of α,α′‐o‐xylenedibromide, formaldehyde and the corresponding 2‐methyl‐4‐, 4‐methyl‐2‐, 2‐pheny‐5‐ and 4‐methyl‐5‐oxazolecarbaldehyde, respectively. Aldehydes were synthesized by using several synthetic approaches. By applying intramolecular photocycloaddition, 2‐methyl‐4‐(2‐vinylstyryl)oxazole afforded, as major product, fused oxazoline‐benzobicyclo[3.2.1]octene with small quantities of 4‐(1,2‐dihydronaphthalen‐2‐yl)‐2‐methyloxazole, as electrocyclization product. Upon irradiation of 4‐methyl‐5‐(2‐vinylstyryl)oxazole, endo‐ and exo‐benzobicyclo[2.1.1]hexene products were formed by [2+2] cycloaddition; this was the first instance of the 1,4‐closure to the bicyclo[2.1.1]hexene skeleton in the 2‐, 4‐, and 5‐oxazole‐stilbene derivatives studied so far. Derivatives 2‐phenyl‐5‐ and 4‐methyl‐2‐(2‐vinylstyryl)oxazole did not react and gave only high‐weight molecular products but were crucial as a comparison in the overall mechanistic study. We have found that, depending on the position of the hexatrienyl moiety in the oxazole ring, as well as on the position of the methyl/phenyl substituents, these new vinylstyryl‐2/4/5‐oxazole derivatives show diverse photochemical behavior.

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Section: Resultsmentioning

confidence: 99%

Versatile Photochemical Reactivity of Diverse Substituted 2‐, 4‐ and 5‐(o‐Vinylstyryl)oxazoles

et al. 2018

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“…Our recent research on the intramolecular photochemical reactions of conjugated thiophene derivatives 1,2 continues the work on furan [3][4][5][6][7][8][9][10] and pyrrole [11][12][13][14][15][16] derivatives of o-divinylbenzenes. Dithiophene derivatives 1, 2 react differently 2 in comparison to previously studied difuran 3 8 and dipyrrole 4 12 derivatives ( Figure 1).…”

Section: Introductionmentioning

confidence: 86%

Photochemical and Thermal Transformations of Thiophene o-Distyrylbenzene Analogues in Acidic Media

Vuk¹,

Marinić²,

Molčanov³

et al. 2012

Croat. Chem. Acta

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Abstract. Intramolecular photochemical reactions of thiophene analogues of o-distyrylbenzene, 2,2'-(o-phenylenedivinylene)dithiophenes (1a,b), 3,3'-(o-phenylenedivinylene)dithiophene (2a) and 3,3'-(o-phenylenedivinylene)dibenzothiophene (2b), were studied in acidic media at low concentrations. A 1,6-and 1,5-ring closure of hexatriene system leading to dihydronaphthalene or indene derivatives, respectively, was observed. (doi: 10.5562/cca2120)

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“…Prior to quantum chemical calculations, molecular geometries were preoptimized by molecular mechanics calculations using the MMX [17] force field; these calculations were performed with the program PCMODEL, version 7.0. [18] Materials: Styrylpyrroles, trans-2-(2-methylstyryl)pyrrole (1), [4] cis-2-(2-methylstyryl)pyrrole (2), [4] trans-N-methyl-2-(2-methylstyryl)-pyrrole (3) [5] and cis-N-methyl-2-(2-methylstyryl)pyrrole (4) [5] were prepared as described in the literature.…”

Section: Methodsmentioning

confidence: 99%

“…We have now investigated by similar techniques some related compounds that are π-isoelectronic with stilbene, namely the 2-styrylpyrroles 1؊6 (Scheme 1). Three of these compounds (1,3,5) have an E-configuration at the central CϭC double bond while the others (2,4,6) are in the Z-configuration. As for the parent stilbene, [1Ϫ3] differences in the stereochemical properties and the electronic structure are of prominent interest.…”

Section: Introductionmentioning

confidence: 99%

Photoelectron Spectra, Electronic Structures, and Conformational Properties of Substituted 2-Styrylpyrroles

et al. 2002

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The UV photoelectron spectra of three pairs of cis/trans-isomers of 2-(2-methylstyryl)pyrroles (1−6) have been recorded and analysed, making use of density functional theory (DFT) calculations at the B3LYP level. Compounds 1 and 2 have no further substituents in the pyrrole ring. In the other compounds the pyrrole ring is substituted by a methyl group in the 1-(3, 4) or 5-position (5, 6). Twisted conformations were calculated for 1−6 in which the toluene ring is generally much more distorted from the plane of the central C=C double bond than the pyrrole ring. In the cis-isomers (2, 4, 6) the torsion angle of the toluene groups amounts to about 50°,

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Synthesis and photochemistry of 2‐styrylpyrroles. Intermolecular photoaddition of pyrroles to a double bond

Cited by 28 publications

References 20 publications

Versatile Photochemical Reactivity of Diverse Substituted 2‐, 4‐ and 5‐(o‐Vinylstyryl)oxazoles

Versatile Photochemical Reactivity of Diverse Substituted 2‐, 4‐ and 5‐(o‐Vinylstyryl)oxazoles

Photochemical and Thermal Transformations of Thiophene o-Distyrylbenzene Analogues in Acidic Media

Photoelectron Spectra, Electronic Structures, and Conformational Properties of Substituted 2-Styrylpyrroles

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