About: Functionalizations of [6]- and [7]helicenes at their most sterically hindered positions

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About: Functionalizations of [6]- and [7]helicenes at their most sterically hindered positions Goto Sponge NotDistinct Permalink

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rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
Description	Although the reactions of enol ethers of aryl methyl ketones with benzoquinone make it easy to prepare nonracemic helicenes that are substituted by hydroxyl groups at their 1,omega-positions, the hydroxyl groups fail to facilitate the introduction of electrophiles ortho to them. However, ethers of [6]- and [7]helicenols prepared in this way, seemingly because of the activation by the alkoxyl groups at the 6-positions, combine with electrophilic reagents to introduce bromines and acyl groups exactly into these positions. Moreover, these bromine and acyl groups can be transformed into other functional groups (including phosphine oxides and acetylenes), the ether functions adjacent to these functional groups can then be removed, and the phenols can be oxidized to quinone-acetals. An alternative way to introduce functional groups next to the phenols is to rearrange their phosphate esters. Two reactions that differentiate the ends of the helicenes are also described. Although the reactions of enol ethers of aryl methyl ketones with benzoquinone make it easy to prepare nonracemic helicenes that are substituted by hydroxyl groups at their 1,omega-positions, the hydroxyl groups fail to facilitate the introduction of electrophiles ortho to them. However, ethers of [6]- and [7]helicenols prepared in this way, seemingly because of the activation by the alkoxyl groups at the 6-positions, combine with electrophilic reagents to introduce bromines and acyl groups exactly into these positions. Moreover, these bromine and acyl groups can be transformed into other functional groups (including phosphine oxides and acetylenes), the ether functions adjacent to these functional groups can then be removed, and the phenols can be oxidized to quinone-acetals. An alternative way to introduce functional groups next to the phenols is to rearrange their phosphate esters. Two reactions that differentiate the ends of the helicenes are also described. (en)
Title	Functionalizations of [6]- and [7]helicenes at their most sterically hindered positions Functionalizations of [6]- and [7]helicenes at their most sterically hindered positions (en)
skos:prefLabel	Functionalizations of [6]- and [7]helicenes at their most sterically hindered positions Functionalizations of [6]- and [7]helicenes at their most sterically hindered positions (en)
skos:notation	RIV/00216224:14310/03:00036035!RIV10-MSM-14310___
http://linked.open...avai/riv/aktivita	V
http://linked.open...avai/riv/aktivity	V
http://linked.open...iv/cisloPeriodika	68
http://linked.open...vai/riv/dodaniDat	2010
http://linked.open...aciTvurceVysledku	Paruch, Kamil
http://linked.open.../riv/druhVysledku	J - Článek v odborném periodiku
http://linked.open...iv/duvernostUdaju	S - Úplné a pravdivé údaje nepodléhající ochraně podle zvláštních právních předpisů
http://linked.open...titaPredkladatele	Masarykova univerzita / Přírodovědecká fakulta
http://linked.open...dnocenehoVysledku	607816
http://linked.open...ai/riv/idVysledku	RIV/00216224:14310/03:00036035
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	helicene; functionalization; sterically hindered (en)
http://linked.open.../riv/klicoveSlovo	functionalization sterically hindered helicene
http://linked.open...odStatuVydavatele	US - Spojené státy americké
http://linked.open...ontrolniKodProRIV	[FA35F78370F7]
http://linked.open...i/riv/nazevZdroje	Journal of Organic Chemistry
http://linked.open...in/vavai/riv/obor	CC
http://linked.open...ichTvurcuVysledku	1 (xsd:int)
http://linked.open...cetTvurcuVysledku	7 (xsd:int)
http://linked.open...UplatneniVysledku	2003
http://linked.open...v/svazekPeriodika	2003
http://linked.open...iv/tvurceVysledku	Paruch, Kamil Katz, Thomas Incarvito, Christopher Rheingold, Arnold Vyklický, Libor Wang, David Zakharov, Lev
issn	0022-3263
number of pages	6 (xsd:int)
http://localhost/t...ganizacniJednotka	14310

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