First Friedel-Crafts Diacylation of a Phenanthrene as the Basis
for an Efficient Synthesis of Nonracemic [7]Helicenes

J 2000

First Friedel-Crafts Diacylation of a Phenanthrene as the Basis for an Efficient Synthesis of Nonracemic [7]Helicenes

PARUCH, Kamil, Thomas KATZ, Christopher INCARVITO, Kin-Chung LAM, Brian RHATIGAN et. al.

Basic information

Original name

First Friedel-Crafts Diacylation of a Phenanthrene as the Basis for an Efficient Synthesis of Nonracemic [7]Helicenes

Name in Czech

First Friedel-Crafts Diacylation of a Phenanthrene as the Basis for an Efficient Synthesis of Nonracemic [7]Helicenes

Authors

PARUCH, Kamil (203 Czech Republic, guarantor), Thomas KATZ (840 United States of America), Christopher INCARVITO (840 United States of America), Kin-Chung LAM (840 United States of America), Brian RHATIGAN (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/00216224:14310/00:00036038

Organization unit

Faculty of Science

Keywords (in Czech)

helicene; preparation; resolution

Keywords in English

helicene; preparation; resolution

Abstract

ORIG CZ

V originále

Reported are the first examples of Friedel-Crafts reactions used to prep. 3,6-diacylphenanthrenes. 9,10-Dimethoxyphenanthrene gives its 3,6-diacetyl deriv. in good yield and in large amts. The ketone's triisopropylsilyl enol ether when combined with 1,4-benzoquinone forms a [7]helicenebisquinone. This bisquinone's redn. product, a bishydroquinone, when combined with methanolic HCl gives the [7]helicene whose peripheral side chains are all methoxyls but whose interior hydroxyls remain. The diastereomeric (1S)-(-)-camphanates can be sepd. by crystn. Their structures, analyzed by X-ray diffraction, demonstrate that the camphanates' lactone functions point away from the ring system when the helicene has the (P) configuration and toward it when the helicene has the (M) configuration. This is because the camphanates' O:C-C-O dihedral angles are, as expected, close to 0 in the former and close to 180 in the latter. Other derivs. of 3,6-diacetylphenanthrene and of [7]helicenebisquinone are prepd., and the crystal structure of one of the latter is analyzed.

In Czech

viz Anotace

Citovat

PARUCH, Kamil, Thomas KATZ, Christopher INCARVITO, Kin-Chung LAM, Brian RHATIGAN and Arnold RHEINGOLD. First Friedel-Crafts Diacylation of a Phenanthrene as the Basis for an Efficient Synthesis of Nonracemic [7]Helicenes. Journal of Organic Chemistry. 2000, vol. 2000, No 65, p. 7602-7608. ISSN 0022-3263.

@article{838542,
   author = {Paruch, Kamil and Katz, Thomas and Incarvito, Christopher and Lam, KinandChung and Rhatigan, Brian and Rheingold, Arnold},
   article_number = {65},
   keywords = {helicene; preparation; resolution},
   language = {eng},
   issn = {0022-3263},
   journal = {Journal of Organic Chemistry},
   title = {First Friedel-Crafts Diacylation of a Phenanthrene as the Basis for an Efficient Synthesis of Nonracemic [7]Helicenes},
   volume = {2000},
   year = {2000}
}

TY  - JOUR
ID  - 838542
AU  - Paruch, Kamil - Katz, Thomas - Incarvito, Christopher - Lam, Kin-Chung - Rhatigan, Brian - Rheingold, Arnold
PY  - 2000
TI  - First Friedel-Crafts Diacylation of a Phenanthrene as the Basis for an Efficient Synthesis of Nonracemic [7]Helicenes
JF  - Journal of Organic Chemistry
VL  - 2000
IS  - 65
SP  - 7602-7608
EP  - 7602-7608
SN  - 00223263
KW  - helicene
KW  - preparation
KW  - resolution
N2  - Reported are the first examples of Friedel-Crafts reactions used to prep. 3,6-diacylphenanthrenes. 9,10-Dimethoxyphenanthrene gives its 3,6-diacetyl deriv. in good yield and in large amts. The ketone's triisopropylsilyl enol ether when combined with 1,4-benzoquinone forms a [7]helicenebisquinone. This bisquinone's redn. product, a bishydroquinone, when combined with methanolic HCl gives the [7]helicene whose peripheral side chains are all methoxyls but whose interior hydroxyls remain. The diastereomeric (1S)-(-)-camphanates can be sepd. by crystn. Their structures, analyzed by X-ray diffraction, demonstrate that the camphanates' lactone functions point away from the ring system when the helicene has the (P) configuration and toward it when the helicene has the (M) configuration. This is because the camphanates' O:C-C-O dihedral angles are, as expected, close to 0 in the former and close to 180 in the latter. Other derivs. of 3,6-diacetylphenanthrene and of [7]helicenebisquinone are prepd., and the crystal structure of one of the latter is analyzed.
ER  -

PARUCH, Kamil, Thomas KATZ, Christopher INCARVITO, Kin-Chung LAM, Brian RHATIGAN and Arnold RHEINGOLD. First Friedel-Crafts Diacylation of a Phenanthrene as the Basis for an Efficient Synthesis of Nonracemic [7]Helicenes. \textit{Journal of Organic Chemistry}. 2000, vol.~2000, No~65, p.~7602-7608. ISSN~0022-3263.

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