Preparation of Chiral Cholestanofluorene and Its Electron-Rich Derivatives for Isolation of a Stable Cation−Radical Salt

Authors

Paromita Debroy, Marquette University
Ruchi Shukla, Marquette University
Sergey V. Lindeman, Marquette UniversityFollow
Rajendra Rathore, Marquette University

Document Type

Article

Language

eng

Publication Date

2007

Publisher

American Chemical Society

Source Publication

The Journal of Organic Chemistry

Source ISSN

0022-3263

Abstract

A simple and practical synthesis of a variety of chiral fluorene derivatives is described where a cholestane moiety is attached to the carbon 9 of the fluorene ring system from readily available starting materials. An appropriately substituted fluorene derivative (i.e., R = OMe) forms a highly colored (chiral) cation−radical that can be isolated as robust hexachloroantimonate salt. Interestingly, the simplest cholestanofluorene (i.e., R = H) can also be transformed into a dibromo derivative (i.e., R = Br), a precursor to the (poly)cholestanofluorenes where the cholestane moieties will serve not only as groups that impart chirality but also allow them to be soluble in common organic solvents. The details of these works are described.

Comments

Accepted version. The Journal of Organic Chemistry, Vol. 72, No. 5 (2007): 1765-1769. DOI. © 2007 American Chemical Society. Used with permission.

Recommended Citation

Debroy, Paromita; Shukla, Ruchi; Lindeman, Sergey V.; and Rathore, Rajendra, "Preparation of Chiral Cholestanofluorene and Its Electron-Rich Derivatives for Isolation of a Stable Cation−Radical Salt" (2007). Chemistry Faculty Research and Publications. 633.
https://epublications.marquette.edu/chem_fac/633