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Statements

Subject Item
n2:RIV%2F00216224%3A14310%2F00%3A00036038%21RIV10-MSM-14310___
rdf:type
n6:Vysledek skos:Concept
dcterms:description
Reported are the first examples of Friedel-Crafts reactions used to prep. 3,6-diacylphenanthrenes. 9,10-Dimethoxyphenanthrene gives its 3,6-diacetyl deriv. in good yield and in large amts. The ketone's triisopropylsilyl enol ether when combined with 1,4-benzoquinone forms a [7]helicenebisquinone. This bisquinone's redn. product, a bishydroquinone, when combined with methanolic HCl gives the [7]helicene whose peripheral side chains are all methoxyls but whose interior hydroxyls remain. The diastereomeric (1S)-(-)-camphanates can be sepd. by crystn. Their structures, analyzed by X-ray diffraction, demonstrate that the camphanates' lactone functions point away from the ring system when the helicene has the (P) configuration and toward it when the helicene has the (M) configuration. This is because the camphanates' O:C-C-O dihedral angles are, as expected, close to 0 in the former and close to 180 in the latter. Other derivs. of 3,6-diacetylphenanthrene and of [7]helicenebisquinone are prepd. Reported are the first examples of Friedel-Crafts reactions used to prep. 3,6-diacylphenanthrenes. 9,10-Dimethoxyphenanthrene gives its 3,6-diacetyl deriv. in good yield and in large amts. The ketone's triisopropylsilyl enol ether when combined with 1,4-benzoquinone forms a [7]helicenebisquinone. This bisquinone's redn. product, a bishydroquinone, when combined with methanolic HCl gives the [7]helicene whose peripheral side chains are all methoxyls but whose interior hydroxyls remain. The diastereomeric (1S)-(-)-camphanates can be sepd. by crystn. Their structures, analyzed by X-ray diffraction, demonstrate that the camphanates' lactone functions point away from the ring system when the helicene has the (P) configuration and toward it when the helicene has the (M) configuration. This is because the camphanates' O:C-C-O dihedral angles are, as expected, close to 0 in the former and close to 180 in the latter. Other derivs. of 3,6-diacetylphenanthrene and of [7]helicenebisquinone are prepd.
dcterms:title
First Friedel-Crafts Diacylation of a Phenanthrene as the Basis for an Efficient Synthesis of Nonracemic [7]Helicenes First Friedel-Crafts Diacylation of a Phenanthrene as the Basis for an Efficient Synthesis of Nonracemic [7]Helicenes
skos:prefLabel
First Friedel-Crafts Diacylation of a Phenanthrene as the Basis for an Efficient Synthesis of Nonracemic [7]Helicenes First Friedel-Crafts Diacylation of a Phenanthrene as the Basis for an Efficient Synthesis of Nonracemic [7]Helicenes
skos:notation
RIV/00216224:14310/00:00036038!RIV10-MSM-14310___
n4:aktivita
n13:V
n4:aktivity
V
n4:cisloPeriodika
65
n4:dodaniDat
n11:2010
n4:domaciTvurceVysledku
n16:1390333
n4:druhVysledku
n10:J
n4:duvernostUdaju
n12:S
n4:entitaPredkladatele
n7:predkladatel
n4:idSjednocenehoVysledku
711316
n4:idVysledku
RIV/00216224:14310/00:00036038
n4:jazykVysledku
n17:eng
n4:klicovaSlova
helicene; preparation; resolution
n4:klicoveSlovo
n5:helicene n5:resolution n5:preparation
n4:kodStatuVydavatele
US - Spojené státy americké
n4:kontrolniKodProRIV
[D43E7CF00CE3]
n4:nazevZdroje
Journal of Organic Chemistry
n4:obor
n14:CC
n4:pocetDomacichTvurcuVysledku
1
n4:pocetTvurcuVysledku
6
n4:rokUplatneniVysledku
n11:2000
n4:svazekPeriodika
2000
n4:tvurceVysledku
Rheingold, Arnold Katz, Thomas Incarvito, Christopher Paruch, Kamil Lam, Kin-Chung Rhatigan, Brian
s:issn
0022-3263
s:numberOfPages
7
n15:organizacniJednotka
14310