ISSN:
1434-4475
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
Abstract Resolution of [2.2]metacyclophane-4,14-dicarboxylic acid (2) was achieved by crystallization of its (+)- and (−)-α-phenylethylamine salts. Chemical correlation with (−)-(S)p-[2.2]metacyclophane-4-caboxylic acid (−)-11 via its monobromo derivative (−)-8 established the absolute configuration of the dicarboxylic acid as (−)-(S)p-2. The key compound (−)-8 was prepared by partial lithiation and subsequent carboxylation of 4,14-dibromo[2.2]metacyclophane (1) and resolution with (−)-phenylethylamine. Recently proposed rules correlating the absolute configurations of planarchiral compounds with theirCD-spectra are discussed and a comparison of the chiroptical properties of 4,14-di- and 4-mono-substituted [2.2]metacyclophanes is presented.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF00909095
