R. H. Wightman

Tricyclic aromatic hydrocarbons. III. Isomerically pure meta-bis-annelated benzenes: a simple synthesis

A short, general synthetic sequence has been developed, involving cycloaddition and a new decarboxylation/aromatization step, to prepare isomerically pure meta-bis-annelated benzenes. Some new bis annelated benzoic acids were isolated as by-products. Examples of a new decar–boxylation of (annelated) benzoic acids catalyzed by Pd/C are reported.

Tricyclic Hydrocarbons. II. Carbon-13 Nuclear Magnetic Resonance Spectroscopy as a Method for Unambiguous Structure Determination

Carbon-13 n.m.r. spectroscopy is demonstrated to be unique as an unambiguous and general method for determining structure in a series of isomeric tricyclic benzenoid hydrocarbons. Observed carbon shieldings for the tricyclic materials are discussed and compared with those for related bicyclic and monocyclic compounds.