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

J 2000

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

PARUCH, Kamil, Libor VYKLICKÝ, Thomas KATZ, Christopher INCARVITO, Arnold RHEINGOLD et. al.

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

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10401 Organic chemistry

Country of publisher

United States of America

Confidentiality degree

není předmětem státního či obchodního tajemství

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

Abstract

ORIG CZ

V originále

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.

In Czech

viz Anotace

Citovat

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.

@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 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. \textit{Journal of Organic Chemistry}. 2000, vol.~2000, No~65, p.~8774-8782. ISSN~0022-3263.

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