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@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 a 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, roč.~2000, č.~65, s.~7602-7608. ISSN~0022-3263.
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