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ASYMMETRIC INDUCTION IN THE SOLID-STATE PHOTOCHEMISTRY OF AMMONIUM-SALTS

TitleASYMMETRIC INDUCTION IN THE SOLID-STATE PHOTOCHEMISTRY OF AMMONIUM-SALTS
Publication TypeJournal Article
Year of Publication1991
AuthorsGudmundsdottir, AD, Scheffer, JR
JournalPhotochemistry and Photobiology
Volume54
Pagination535-538
Date PublishedOct
Type of ArticleArticle
ISBN Number0031-8655
KeywordsPHOTOISOMERIZATION
Abstract

A general approach to using crystal chirality in asymmetric synthesis is described. An example consists of the preparation of crystalline salts of dimethyl 9-amino-9,10-ethenoanthracene-11,12-dicarboxylate (1) with optically active sulfonic acids. Photolysis of the salts in the solid state generates a product that has chiral centers in the amine-containing portion of the molecule (di-pi-methane photorearrangement). The optical activity in the photoproduct was determined by polarimetry and NMR chiral shift reagent analysis, which revealed enantiomeric excesses ranging from 30 to 68% depending on the optically active sulfonic acid employed. In contrast to the results in the crystalline state, irradiation of the salts in acetonitrile gave racemic photoproduct.

URL<Go to ISI>://A1991GD93400005