A photochemical entry to spirobenzofurans
TL;DR: Synthesis of spirobenzofurans based on photochemical ''δ'' hydrogen abstraction was reported in this article, where the synthesis was carried out in a laboratory environment.
About: This article is published in Tetrahedron Letters.The article was published on 1992-04-14. It has received 15 citations till now. The article focuses on the topics: Hydrogen atom abstraction.
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27 citations
TL;DR: The photochemistry of a series of 9,10-anthraquinones with multiple benzyloxy substituents was investigated and indicates the importance of considering the medium and photoredox behavior in anthraquinone photochemistry.
Abstract: The photochemistry of a series of 9,10-anthraquinones with multiple benzyloxy substituents was investigated. In polar solvent, the expected Blankespoor oxidative cleavage reaction is the major reaction pathway, but in most cases, several minor products were observed. In nonpolar solvents, the abundance of these minor products increases dramatically. Four types of product were observed with the favored reaction pathway shifting with minor changes in substitution on the anthraquinone. Several types of product require cleavage of the C−O bond on the benzyloxy group and, apparently, follow a photo-Claisen-type mechanism. Others involve the expected 1,5-diradical but do not exhibit the single-electron transfer usually observed in the Blankespoor-type reaction. The results indicate the importance of considering the medium and photoredox behavior in anthraquinone photochemistry.
19 citations
TL;DR: In this article, a direct photochemical route to the synthesis of spirobenzopyranochromones via H-abstraction was reported, and the synthesis was shown to work well.
13 citations
TL;DR: In this article, a photoisomerization of allyl ethers is described for the synthesis of vinyl ethers through the photoisomersization of the allyl acid and allyl dioxide.
13 citations
TL;DR: In this article, the synthesis of novel cyclophanes containing both benzo[1,2-b:5,4-b′]difuran and naphthalene rings has been developed.
Abstract: Facile routes for the synthesis of novel cyclophanes 1a, b containing both benzo[1,2-b:5,4-b′]difuran and naphthalene rings have been developed. Irradiation of 1,5-dibenzoyl-2,4-dialkoxybenzene derivatives 3a, b with a 350 nm mercury lamp followed by dehydration afforded benzo[1,2-b:5,4-b′]difuran ring systems 5a, b. The cyclophanes 1a, b were prepared either from the ether-forming reaction between the preformed benzodifuran ring derivatives 5a, b and 2,7-dihydroxynaphthalene, or from the photocyclization–dehydration
reaction of the macrocycles 6a, b prepared by reacting 1,5-dibenzoyl-2,4-bis(ω-bromoalkoxy)benzene with 2,7-dihydroxynaphthalene. The cyclophanes 2a, b containing two benzo[1,2-b:5,4-b′]difuran and two naphthalene moieties were obtained as minor products.
13 citations
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41 citations
TL;DR: In this paper, the Synthese der Titelverbindung (V) erfolgt ausgehend vom Acetat (Ib) der Verbindung (Ia) uber die Stufen (IIa), (IIb) [aus(IIa) mit Thiophenol], (IIc) mit (IV).
Abstract: Die Synthese der Titelverbindung (V) erfolgt ausgehend vom Acetat (Ib) der Verbindung (Ia) uber die Stufen (IIa), (IIb) [aus (IIa) mit Thiophenol], (IIc) mit (IV).
25 citations
25 citations