A Versatile Preparation of Geländer-Type p-Terphenyls from a Readily Available Diacetylenic Precursor

Authors

Matthew J. Modjewski, Marquette University
Sergey V. Lindeman, Marquette UniversityFollow
Rajendra Rathore, Marquette University

Document Type

Article

Language

eng

Format of Original

4 p.

Publication Date

2009

Publisher

American Chemical Society

Source Publication

Organic Letters

Source ISSN

1523-7060

Abstract

A series of doubly bridged p-terphenyls (4) have been synthesized utilizing a facile three-step synthesis starting from the readily available diacetylenic precursor (1) in excellent overall yields, and their structures were confirmed by 1H/13C NMR spectroscopy as well as by X-ray crystallography. The racemization barrier between the meso and chiral atropisomers of one of the derivatives of 4 was found to be ∼12 kcal/mol by variable-temperature NMR spectroscopy. The versatility of the protocol developed herein was further demonstrated by the preparation of a quadruply bridged penta-p-phenylene derivative.

Comments

Accepted version. Organic Letters, Vol. 11, No. 20 (2009): 4656-4659. DOI. © 2009 American Chemical Society. Used with permission.

Recommended Citation

Modjewski, Matthew J.; Lindeman, Sergey V.; and Rathore, Rajendra, "A Versatile Preparation of Geländer-Type p-Terphenyls from a Readily Available Diacetylenic Precursor" (2009). Chemistry Faculty Research and Publications. 542.
https://epublications.marquette.edu/chem_fac/542