About: Acidified Alcohols as Agents to Introduce and Exchange Alkoxyls on the Periphery of Helicenes     Goto   Sponge   NotDistinct   Permalink

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  • Alcs. contg. HCl transform the hydroquinone redn.-products of helicenebisquinones into p-alkoxyphenols that have the alkoxyls specifically on the peripheries of the helixes. The reactions are quick, and the yields are high. Alkoxyls at the 6-position are replaced also, but only after 2 h at 60 C, not after the 5 min at 25 C sufficient to replace the peripheral hydroxyls of the hydroquinones. After the remaining inside hydroxyls of a dihydroxytetramethoxy[6]helicene prepd. by this procedure were converted into camphanates, one diastereomer crystallizes from soln., allowing an enantiomer resoln. to be carried out on a large scale. By then simply re-applying the procedure with alc. acid, a variety of resolved dihydroxytetraalkoxy[6]helicenes can be prepd. in excellent yields without resoln. procedures having to be developed for each. Similar procedures are effective when applied to a [7]carbohelicene.
  • Alcs. contg. HCl transform the hydroquinone redn.-products of helicenebisquinones into p-alkoxyphenols that have the alkoxyls specifically on the peripheries of the helixes. The reactions are quick, and the yields are high. Alkoxyls at the 6-position are replaced also, but only after 2 h at 60 C, not after the 5 min at 25 C sufficient to replace the peripheral hydroxyls of the hydroquinones. After the remaining inside hydroxyls of a dihydroxytetramethoxy[6]helicene prepd. by this procedure were converted into camphanates, one diastereomer crystallizes from soln., allowing an enantiomer resoln. to be carried out on a large scale. By then simply re-applying the procedure with alc. acid, a variety of resolved dihydroxytetraalkoxy[6]helicenes can be prepd. in excellent yields without resoln. procedures having to be developed for each. Similar procedures are effective when applied to a [7]carbohelicene. (en)
Title
  • Acidified Alcohols as Agents to Introduce and Exchange Alkoxyls on the Periphery of Helicenes
  • Acidified Alcohols as Agents to Introduce and Exchange Alkoxyls on the Periphery of Helicenes (en)
skos:prefLabel
  • Acidified Alcohols as Agents to Introduce and Exchange Alkoxyls on the Periphery of Helicenes
  • Acidified Alcohols as Agents to Introduce and Exchange Alkoxyls on the Periphery of Helicenes (en)
skos:notation
  • RIV/00216224:14310/00:00036036!RIV10-MSM-14310___
http://linked.open...avai/riv/aktivita
http://linked.open...avai/riv/aktivity
  • V
http://linked.open...iv/cisloPeriodika
  • 65
http://linked.open...vai/riv/dodaniDat
http://linked.open...aciTvurceVysledku
http://linked.open.../riv/druhVysledku
http://linked.open...iv/duvernostUdaju
http://linked.open...titaPredkladatele
http://linked.open...dnocenehoVysledku
  • 703861
http://linked.open...ai/riv/idVysledku
  • RIV/00216224:14310/00:00036036
http://linked.open...riv/jazykVysledku
http://linked.open.../riv/klicovaSlova
  • helicene; alkoxyl; diastereomer; separation (en)
http://linked.open.../riv/klicoveSlovo
http://linked.open...odStatuVydavatele
  • US - Spojené státy americké
http://linked.open...ontrolniKodProRIV
  • [28D855CC3A99]
http://linked.open...i/riv/nazevZdroje
  • Journal of Organic Chemistry
http://linked.open...in/vavai/riv/obor
http://linked.open...ichTvurcuVysledku
http://linked.open...cetTvurcuVysledku
http://linked.open...UplatneniVysledku
http://linked.open...v/svazekPeriodika
  • 2000
http://linked.open...iv/tvurceVysledku
  • Paruch, Kamil
  • Dreher, Spencer
  • Katz, Thomas
issn
  • 0022-3263
number of pages
http://localhost/t...ganizacniJednotka
  • 14310
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