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@article{838534,
author = {Paruch, Kamil and Vyklický, Libor and Wang, David and Katz, Thomas and Incarvito, Christopher and Zakharov, Lev and Rheingold, Arnold},
article_number = {68},
keywords = {helicene; functionalization; sterically hindered},
language = {eng},
issn = {0022-3263},
journal = {Journal of Organic Chemistry},
title = {Functionalizations of [6]- and [7]helicenes at their most sterically hindered positions},
volume = {2003},
year = {2003}
}
TY - JOUR
ID - 838534
AU - Paruch, Kamil - Vyklický, Libor - Wang, David - Katz, Thomas - Incarvito, Christopher - Zakharov, Lev - Rheingold, Arnold
PY - 2003
TI - Functionalizations of [6]- and [7]helicenes at their most sterically hindered positions
JF - Journal of Organic Chemistry
VL - 2003
IS - 68
SP - 8539-8544
EP - 8539-8544
SN - 00223263
KW - helicene
KW - functionalization
KW - sterically hindered
N2 - Although the reactions of enol ethers of aryl methyl ketones with benzoquinone make it easy to prepare nonracemic helicenes that are substituted by hydroxyl groups at their 1,omega-positions, the hydroxyl groups fail to facilitate the introduction of electrophiles ortho to them. However, ethers of [6]- and [7]helicenols prepared in this way, seemingly because of the activation by the alkoxyl groups at the 6-positions, combine with electrophilic reagents to introduce bromines and acyl groups exactly into these positions. Moreover, these bromine and acyl groups can be transformed into other functional groups (including phosphine oxides and acetylenes), the ether functions adjacent to these functional groups can then be removed, and the phenols can be oxidized to quinone-acetals. An alternative way to introduce functional groups next to the phenols is to rearrange their phosphate esters. Two reactions that differentiate the ends of the helicenes are also described.
ER -
PARUCH, Kamil, Libor VYKLICKÝ, David WANG, Thomas KATZ, Christopher INCARVITO, Lev ZAKHAROV a Arnold RHEINGOLD. Functionalizations of [6]- and [7]helicenes at their most sterically hindered positions. \textit{Journal of Organic Chemistry}. 2003, roč.~2003, č.~68, s.~8539-8544. ISSN~0022-3263.
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