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Unexpected racemization in the series of 4,5-disubstituted [2.2]paracyclophanes

Unexpected racemization in the series of 4,5-disubstituted [2.2]paracyclophanes 2702 Russian Chemical Bulletin, International Edition, Vol. 54, No. 11, pp. 2702—2703, November, 2005 Letters to the Editor Unexpected racemization in the series of 4,5disubstituted [2.2]paracyclophanes R. P. Zhuravsky, V. I. Rozenberg, E. V. Sergeeva, and E. V. Vorontsov A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991 Moscow, Russian Federation. Fax: +7 (495) 135 5085. Email: ineosghkl@yandex.ru During the development of approaches to regio from the enantiomers of 4hydroxy[2.2]paracyclophane. selective synthesis of novel types of planar chiral ligands Unexpectedly, the aforementioned sequence of transfor from [2.2]paracyclophane, we studied the possibility of mations of compound (S)2 gave products 3, 4, and 1 obtaining 5hydroxy4methoxy[2.2]paracyclophane (1), with nearly zero optical rotation values and HPLC analy a chiral analog of guaiacol. For this purpose, we carried sis of compound 1 on a chiral phase revealed its racemic out ortholithiation of racemic 4carbamoyloxy[2.2]para nature. Cleavage of the ethano bridges in paracyclophane s 2 cyclophane (2) (Bu Li/THF, –78 °C) followed by is impossible under the reaction conditions used, which treatment of the reaction mixture with B(OMe) and was experimentally confirmed by the retained optical ro oxidation of the intermediate boronic derivative with tation value of partially http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Russian Chemical Bulletin Springer Journals

Unexpected racemization in the series of 4,5-disubstituted [2.2]paracyclophanes

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References (7)

Publisher
Springer Journals
Copyright
Copyright © 2005 by Springer Science+Business Media, Inc.
Subject
Chemistry; Inorganic Chemistry; Organic Chemistry; Chemistry/Food Science, general
ISSN
1066-5285
eISSN
1573-9171
DOI
10.1007/s11172-006-0180-8
Publisher site
See Article on Publisher Site

Abstract

2702 Russian Chemical Bulletin, International Edition, Vol. 54, No. 11, pp. 2702—2703, November, 2005 Letters to the Editor Unexpected racemization in the series of 4,5disubstituted [2.2]paracyclophanes R. P. Zhuravsky, V. I. Rozenberg, E. V. Sergeeva, and E. V. Vorontsov A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991 Moscow, Russian Federation. Fax: +7 (495) 135 5085. Email: ineosghkl@yandex.ru During the development of approaches to regio from the enantiomers of 4hydroxy[2.2]paracyclophane. selective synthesis of novel types of planar chiral ligands Unexpectedly, the aforementioned sequence of transfor from [2.2]paracyclophane, we studied the possibility of mations of compound (S)2 gave products 3, 4, and 1 obtaining 5hydroxy4methoxy[2.2]paracyclophane (1), with nearly zero optical rotation values and HPLC analy a chiral analog of guaiacol. For this purpose, we carried sis of compound 1 on a chiral phase revealed its racemic out ortholithiation of racemic 4carbamoyloxy[2.2]para nature. Cleavage of the ethano bridges in paracyclophane s 2 cyclophane (2) (Bu Li/THF, –78 °C) followed by is impossible under the reaction conditions used, which treatment of the reaction mixture with B(OMe) and was experimentally confirmed by the retained optical ro oxidation of the intermediate boronic derivative with tation value of partially

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Russian Chemical Bulletin – Springer Journals

Published: Apr 7, 2006

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