Chirality and conformational changes in 4,5-diaryltriphenylenes

Tinnemans, A. H. A.; Laarhoven, W. H.

doi:10.1016/0040-4020(79)80041-1

Cited by 18 publications

(13 citation statements)

References 6 publications

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“…To our delight, the ortho -methyl-substituted aryl alkyne afforded the product 3q in good yield as well. Due to the higher rotational barrier,17 product 3q exists in solution as a mixture of multiple rotamers as confirmed by variable temperature 1 H NMR and 1D NOE experiments 18. Even the more hindered substrate (2,4,6-trimethylphenyl)acetylene underwent bisannulation to give the target product 3r in 7% yield.…”

Section: Resultsmentioning

confidence: 87%

“…The configurational stability of 4,5-diarylphenanthrene with ortho - or meta -substituents in the aryl moiety (such as 3m–r ) are comparatively higher than 3a (Scheme 3). 17 A kinetic study of the thermal racemization of 3n was performed, corresponding to a racemization barrier of 126 kJ mol –1 at 100 °C. Using the solution of highly enantioenriched 3n in 1,2-dichloroethane, only a small drop in e.r.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis of sterically hindered 4,5-diarylphenanthrenes via acid-catalyzed bisannulation of benzenediacetaldehydes with alkynes

Yagi

Itami

2019

Chem. Sci.

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Section: Resultsmentioning

confidence: 87%

Section: Resultsmentioning

confidence: 99%

Synthesis of sterically hindered 4,5-diarylphenanthrenes via acid-catalyzed bisannulation of benzenediacetaldehydes with alkynes

Yagi

Itami

2019

Chem. Sci.

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“…Similarly, 4,5-diphenyl-(21), 4-(3,5-dimethylphenyl)-5-phenyl- (22), and 4,5-bi(3,5-dimethylphenyl)triphenylene (23) (Fig. 6) were also synthesized from the corresponding 1-buten-3-ynes [33]. Monobromination of 22 and 23 produced 24 and 25, respectively.…”

Section: 5-diarylphenanthrenesmentioning

confidence: 99%

Twisted Arenes

Wang

2012

Polyarenes I

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The nonbonded steric interactions of substituents at the crowded C4 and C5 positions of phenanthrene cause the aromatic system to twist out of planarity. Similarly, the presence of substituents at the C1 and C12 positions of benzo[c]phenanthrene and at the C1 and C14 positions of dibenzo[c,g]phenanthrene are responsible for the helical twists of the aromatic frameworks. Highly substituted acenes, such as octamethylnaphthalene and decaphenylanthracene, also exhibit substantial end-to-end twists. The X-ray structures of these compounds allow direct measurements of the extent of the structural distortions. The configurational stabilities of many twisted arenes have also been determined.

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“…Zuordnung der ^-NM R-Signale von 2a zur Allyl-l,5-hexadien-Struktur 2a und zur Tris(allyl)-Struktur 2'a (vergl. [13,14] M esitylacetylen [15], (C H 3)3SiH [16], B ortriiodid [17] und N i(C 3H 5) 2 [18] w urden nach L iteraturvorschrift hergestellt. …”

Section: He'unclassified

Synthese und Struktur von benzylsubstituierten Derivaten des Dinickel-Tripeldeckerkomplexes μ-η⁵,η⁵(2,3–Dihydro–1,3-diborolyl)-(η³–allyl)(η⁴–1,5–hexadien) dinickel / Synthesis and Structure of Benzyl Substituted Derivatives of the Dinickel Triple-Decker Complex μ–η⁵, η⁵–(2 ,3–Dihydro–1,3 -diborolyl)– (η³–allyl)(η⁴– 1,5 -hexadiene)dinickel

Siebert¹,

Huck²,

Pritzkow³

2001

Zeitschrift Für Naturforschung B

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Synthesis and S tructure o f B enzyl S ubstituted D erivatives of the D inickel T riple-D ecker C om plex ,w-?75,?75-(2 ,3 -D ih y d ro -l,3 -diborolyl)-(?73-allyl)(774-l ,5 -hexadiene)dinickel W alter Siebert, Stefan H uck und H an s Pritzkow Nickel, //-775,?75-(2 ,3-Dihydro-l,3-diborolyl)(?73-allyl)(?74-l,5-hexadiene)dinickel, Polydecker ComplexesHydroboration of phenyl-and mesitylethyne with in situ formed HBC12 leads to an isome ric mixture of l,l-bis(dichloroboryl)-2-phenylethane (4a) and l,l-bis(dichloroboryl)-l-phenylethane (4b) (ratio 3 : 1) and regioselectively to l,l-bis(dichloroboryl)-2-mesitylethane (4c). Treatment of 4a/b and 4c with BI3 gives the corresponding tetraiodo compounds 5, which undergo redox reactions with butyne-2 to form the l,3-diiodo-4,5-dimethyl-2,3-dihydro-l,3diborole derivatives 6a/b and 6c. Reactions of the diiodo-l,3-diboroles with AlMe3 or LiMe result in the formation of the very air-sensitive pentaorganyl-l,3-diboroles la, lc and the hexaorganyl-l,3-diborole lb.The mixture of la/b as well as lc react with bis(?/3-allyl)nickel to give black products, which are chromatographed on silica with hexane as eluent. The brown solids were recrystallized from pentane to give the light-brown crystals of i M-j/5,7;5-[2-benzyl-l,3 ,4 ,5 -tetramethyl-2 ,3-dihydrol,3-diborolyl](/73-allyl)(»74-l,5-hexadiene)dinickel (2a, 34%) and //-?/5,»75-[2-(2 ,4 ,6-trimethylbenzyl)-l,3 ,4 ,5-tetramethyl-2,3-dihydro-l,3-diborolyl](?73-allyl)(?74-l,5-hexadiene)dinickel (2c, 43%). lb does not react with Ni(C3H5)2 to form any triple-decker. The compositions of the new compounds follow from spectroscopic and analytical data, and from X-ray structure analyses of 6a and of 2a. The structure of the ?74-l,5-hexadiene-?73-allyl-dinickel triple-decker 2a finally disproved the alternative tris(allyl)dinickel arrangement.

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Chirality and conformational changes in 4,5-diaryltriphenylenes

Cited by 18 publications

References 6 publications

Synthesis of sterically hindered 4,5-diarylphenanthrenes via acid-catalyzed bisannulation of benzenediacetaldehydes with alkynes

Synthesis of sterically hindered 4,5-diarylphenanthrenes via acid-catalyzed bisannulation of benzenediacetaldehydes with alkynes

Twisted Arenes

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