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@article{838544,
author = {Paruch, Kamil and Vyklický, Libor and Katz, Thomas and Incarvito, Christopher and Rheingold, Arnold},
article_number = {65},
keywords = {helicene; Miura; preparation; optical properties},
language = {eng},
issn = {0022-3263},
journal = {Journal of Organic Chemistry},
title = {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},
volume = {2000},
year = {2000}
}
TY - JOUR
ID - 838544
AU - Paruch, Kamil - Vyklický, Libor - Katz, Thomas - Incarvito, Christopher - Rheingold, Arnold
PY - 2000
TI - 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
JF - Journal of Organic Chemistry
VL - 2000
IS - 65
SP - 8774-8782
EP - 8774-8782
SN - 00223263
KW - helicene
KW - Miura
KW - preparation
KW - optical properties
N2 - 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.
ER -
PARUCH, Kamil, Libor VYKLICKÝ, Thomas KATZ, Christopher INCARVITO a 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. \textit{Journal of Organic Chemistry}. 2000, roč.~2000, č.~65, s.~8774-8782. ISSN~0022-3263.
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