Attempts to functionalize polycyclic quinones using lithium diisopropylamide as a base led to the unexpected formation of acenes. This reaction proceeds by electron transfer from the base to the electron deficient quinone, whose radical anion can react with a variety of electrophiles. Siloxy derivatives synthesized by this method could be easily isolated but showed poor photostability. In situ reduced intermediate generation is a convenient approach to functionalization of oxidatively unstable hydroquinones.
|Number of pages||4|
|State||Published - Sep 18 2020|
Bibliographical noteFunding Information:
Support for this work was provided by the U.S. Department of Energy, Office of Basic Energy Sciences (ERW7404), and the MRI program of the National Science Foundation (Grants CHE-0319176 and CHE-1625732).
© 2020 American Chemical Society.
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry