Syntheses of dibenzofuran-type and dinaphthofuranquinone-type fused furans.

Ishikawa, Seiichi; Hinoshita, Hirotaka; Takagi, Makoto; Ueno, Keihei

doi:10.1246/nikkashi.1988.743

Cited by 7 publications

(2 citation statements)

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“…After stirring for 10 h and following the procedure of Kyba et al (1977) for the isolation of (R)-2,2'-bis(5-hydroxy-3-oxa-1-pentyloxy)-1,1'-binapthyl, a small quantity (ca 0.05 g) of golden-yellow crystals of the title compound was isolated. Another synthesis of (I) has been reported previously (Ishikawa, Hinoshita, Tagaki & Ueno, 1988).…”

Section: Methodsmentioning

confidence: 99%

A Naphthofuranoquinone

Farrugia¹,

Scott²,

Peacock³

1996

Acta Crystallogr C

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The title compound, dinaphtho[2,1-b:2',3'-d]furan-8,13-(8H,13H)-dione, C20Hi003, was prepared in low yield from the reaction of (2-chloroethoxy)ethyl 2-tetrahydropyranyl ether with (R)-l,l'-binapth-2,2'-ol. The ring system is virtually planar [the largest° deviation from the mean plane of the ring is 0.116 (4)A for atom C13] despite the O13.Abstract The title compound, C9HI2N405, adopts a distinct ring-twisted conformation defined by nearly orthogonal bridgehead torsion angles [C16---C15--C14---N19 -90. 1 (2) and C26--C25--C24--N29 -87.8 (2)°]. The antiperiplanar array [C 17---014--C 14---N 19 -15 8.0 (2)

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Section: Methodsmentioning

confidence: 99%

A Naphthofuranoquinone

Farrugia¹,

Scott²,

Peacock³

1996

Acta Crystallogr C

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“…This reaction was applied to other ortho ‐dihydroxybiaryls to generate a variety of helicenes. Ueno and coworkers systematically examined this type of condensation reaction where naphthol is replaced with various aryl alcohols [3] . Perylene‐fused furan 3 was prepared from corresponding bis(hydroxyperylenol) [4] and a more π‐expanded furan, e. g ., the hexabenzocoronene‐annulated furan 4 , was reported (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

Pyrene‐Fused Furan: Simple Synthesis of π‐Expanded Heterohelicene

et al. 2022

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Treatment of p‐toluenesulfonic acid on bipyrenol in PhCl gave a pyrene‐fused furan. The expansion of the molecule induced a narrow HOMO‐LUMO gap, multiple redox processes showing both oxidation and reduction, and a bathochromic shift in the absorption spectrum. A small Stokes shift was caused by the rigidity of the molecule. The structures and electronic states were estimated by theoretical considerations. We found that the heteroatom containing a [5]helicene molecule shows racemization through a planar transition state.

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