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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. vol. 2000, No 65, p. 7602-7608. ISSN 0022-3263. 2000.

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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
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/00216224:14310/00:00036038
Organization unit	Faculty of Science
Keywords (in Czech)	helicene; preparation; resolution
Keywords in English	helicene; preparation; resolution
Tags	helicene, Preparation, RESOLUTION
Changed by	Changed by: doc. Mgr. Kamil Paruch, Ph.D., učo 108413. Changed: 25/6/2009 15:32.

Abstract
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.

Abstract

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.

Abstract (in Czech)
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