PARUCH, Kamil, Libor VYKLICKÝ, Thomas KATZ, Christopher INCARVITO and Arnold RHEINGOLD. Expeditious Procedure To Synthesize Ethers and Esters of Tri- and Tetrahydroxy[6]helicenebisquinones from the Dye-Intermediates Disodium 4-Hydroxy- and 4,5-Dihydroxynaphthalene-2,7-disulfonates. Journal of Organic Chemistry. 2000, vol. 2000, No 65, p. 8774-8782. ISSN 0022-3263.
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Basic information
Original name Expeditious Procedure To Synthesize Ethers and Esters of Tri- and Tetrahydroxy[6]helicenebisquinones from the Dye-Intermediates Disodium 4-Hydroxy- and 4,5-Dihydroxynaphthalene-2,7-disulfonates
Name in Czech Expeditious Procedure To Synthesize Ethers and Esters of Tri- and Tetrahydroxy[6]helicenebisquinones from the Dye-Intermediates Disodium 4-Hydroxy- and 4,5-Dihydroxynaphthalene-2,7-disulfonates
Authors PARUCH, Kamil (203 Czech Republic, guarantor), Libor VYKLICKÝ (203 Czech Republic), Thomas KATZ (840 United States of America), Christopher INCARVITO (840 United States of America) and Arnold RHEINGOLD (840 United States of America).
Edition Journal of Organic Chemistry, 2000, 0022-3263.
Other information
Original language English
Type of outcome Article in a journal
Field of Study 10401 Organic chemistry
Country of publisher United States of America
Confidentiality degree is not subject to a state or trade secret
Impact factor Impact factor: 3.689
RIV identification code RIV/00216224:14310/00:00036039
Organization unit Faculty of Science
Keywords (in Czech) helicene; Miura; preparation; optical properties
Keywords in English helicene; Miura; preparation; optical properties
Tags helicene, Miura, Optical properties, Preparation
Changed by Changed by: doc. Mgr. Kamil Paruch, Ph.D., učo 108413. Changed: 25/6/2009 15:37.
Abstract
A procedure is described for synthesizing appreciable quantities of both the tetradodecyloxy[6]helicenebisquinone I (R = dodecyl), which exhibits unique optical properties but previously was difficult to prep., and a variety of analogs. The synthesis starts from disodium 4,5-dihydroxynaphthalene-2,7-disulfonate, the com. available dye-intermediate known as chromotropic acid. It gives enantiopure I [R = (Me2CH)3Si] whose silyl groups can be replaced by dodecyl and hexanoyl groups. The same procedure applied to disodium 4-hydroxynaphthalene-2,7-disulfonate, also an inexpensive, com. available chem., works equally well to produce the corresponding mols. that have one fewer side chain. Key steps are the use of tosyl groups to protect phenols and of a method described seven years ago by Satoh, Itoh, Miura, and Nomura to transform the sulfonic acid functions to iodides. The structure of tetra-(1S)-camphanate II [R1 = (Me2CH)3Si; R2 = (1S)-camphanoyl], the ester of the redn. product of (-)-I [R = (Me2CH)3Si], was analyzed by X-ray diffraction. It shows the abs. configurations and supports the presumed basis for the rule that the (1S)-camphanates of (P)-helicen-1-ols are more polar than their (M)-diastereomers.
Abstract (in Czech)
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