The Effect of Bulky Substituents on the Formation of Symmetrically Trisubstituted Triptycenes

Chmiel J, Heesemann I, Mix A, Neumann B, Stammler H-G, Mitzel NW (2010)
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 2010(20): 3897-3907.

Journal Article | Published | English

No fulltext has been uploaded

Abstract
A series of 1,8-dichloroanthracene precursor molecules with substituents in C-10 position of different steric demand (cyclohexyl, tert-butyl, methyl, isopropyl, n-butyl, phenyl, benzyl, trimethylsilylethinyl) were synthesised and subjected to electrocyclic cycloadditions with chlorobenzyne generated from 3-chloroanthranilic acid. The aim was to steer the regioselectivity of the addition reaction by the steric repulsion between this C-10 substituent and the chlorine substituent at the benzyne intermediate. With H as C-10 substituent the reaction leads to 23% syn and 77% anti form. With the small methyl group a syn/anti ratio of 37:63 was achieved. Contrary to our expectations the large C-10 substituent tert-butyl leads to 100% selectivity for the anti form. The best results were achieved for the C-10 substituent n-butyl with a syn/anti ratio of 40:60. The crystal structures of five 1,8-dichloroanthracenes with C-10 substituents were determined, namely those with tert-butyl, cyclohexyl, n-butyl and phenyl groups. As expected the backbone of the tert-butyl compound shows marked distortion of the planarity. Additionally, the crystal structures of three triptycenes were determined, namely those of the syn compound 1,8,13-trichlorotriptycene and those of the anti compounds 10-tert-butyl-1,8,16-trichlorotriptycene and 1,8,16-trichloro-10-methyltriptycene.
Publishing Year
ISSN
eISSN
PUB-ID

Cite this

Chmiel J, Heesemann I, Mix A, Neumann B, Stammler H-G, Mitzel NW. The Effect of Bulky Substituents on the Formation of Symmetrically Trisubstituted Triptycenes. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. 2010;2010(20):3897-3907.
Chmiel, J., Heesemann, I., Mix, A., Neumann, B., Stammler, H. - G., & Mitzel, N. W. (2010). The Effect of Bulky Substituents on the Formation of Symmetrically Trisubstituted Triptycenes. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010(20), 3897-3907.
Chmiel, J., Heesemann, I., Mix, A., Neumann, B., Stammler, H. - G., and Mitzel, N. W. (2010). The Effect of Bulky Substituents on the Formation of Symmetrically Trisubstituted Triptycenes. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 2010, 3897-3907.
Chmiel, J., et al., 2010. The Effect of Bulky Substituents on the Formation of Symmetrically Trisubstituted Triptycenes. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010(20), p 3897-3907.
J. Chmiel, et al., “The Effect of Bulky Substituents on the Formation of Symmetrically Trisubstituted Triptycenes”, EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, vol. 2010, 2010, pp. 3897-3907.
Chmiel, J., Heesemann, I., Mix, A., Neumann, B., Stammler, H.-G., Mitzel, N.W.: The Effect of Bulky Substituents on the Formation of Symmetrically Trisubstituted Triptycenes. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. 2010, 3897-3907 (2010).
Chmiel, Jasmin, Heesemann, Ingo, Mix, Andreas, Neumann, Beate, Stammler, Hans-Georg, and Mitzel, Norbert W. “The Effect of Bulky Substituents on the Formation of Symmetrically Trisubstituted Triptycenes”. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 2010.20 (2010): 3897-3907.
This data publication is cited in the following publications:
This publication cites the following data publications:

Export

0 Marked Publications

Open Data PUB

Web of Science

View record in Web of Science®

Search this title in

Google Scholar