The arene–alkene photocycloaddition

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The arene–alkene photocycloaddition

In the presence of an alkene, three different modes of photocycloaddition with benzene derivatives can occur; the [2 + 2] or ortho, the [3 + 2] or meta, and the [4 + 2] or para photocycloaddition. This short review aims to demonstrate the synthetic power of these photocycloadditions.

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A remarkable double [3 + 2] photocycloaddition reaction that results in the formation of fenestrane 2 from aromatic acetal 1 is reported. During the formation of 2, four carbon-carbon bonds, five new rings, and seven new stereocenters are created in a one-pot process. The reaction occurs in a sequential manner from the linear meta photocycloadduct 3, while the angular meta photocycloadduct 4 un...

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The Inter- and Intramolecular Photocycloaddition of Ethylenes to Aromatic Compounds

Dienophilic ethylenes yield solely ortho photocycloadducts with benzene whereas alkenes and enol ethers give products arising from both ortho and meta cycloaddition. The relative efficiencies of the twoprocesses are largely predictable and this combined with reasonable chemical and quantum yields make these photoreactions realistic synthetic procedures towards bicyclo[4.2.Oloctane and tricyclo[...

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Conformationally restricted pyrrolidines by intramolecular [2+2] photocycloaddition reactions.

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Biradical intermediate in the [2 + 2] photocycloaddition of dienes and alkenes to [60]fullerene.

The photocycloaddition of vinylcyclopropanes to C60 yields stereospecifically a five-membered [60]fullerene adduct. These results suggest a biradical intermediate of the [2 + 2] photocycloaddition between dienes or arylalkenes and C60. An electron transfer between the triplet excited state of C60 and the unsaturated substrates precedes the formation of the intermediate.

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ژورنال

عنوان ژورنال: Beilstein Journal of Organic Chemistry

سال: 2011

ISSN: 1860-5397

DOI: 10.3762/bjoc.7.61