m-Benzyne and p-Benzyne

Abstract

Angeles, and returned to the University of Heidelberg in 1984. After completing his Habilitation in 1989, he joined the Institute of Organic Chemistry at the University of Braunschweig as Associate Professor, and since 1993 he has been Full Professor of Chemistry at the University of Bochum. His research interest in the field of physical organic chemistry is the characterization of reactive intermediates using matrix isolation spectroscopy and time-resolved techniques.

Do Bicyclic Forms ofm- andp-Benzyne Exist?

“…Here pyridine attacks the threemembered ring of 6 with formation of the intermediate 7 with subsequent formation of the m-benzyne 8. The driving force for this reaction is in part due to the formation of the unusually stable bis(pyrdinium)phenide intermediate (7). [32] …”

“…[5,6] More recently the emphasis has been on low-temperature preparation of these reactive species and their characterization by infrared spectroscopy. [7] o-Benzyne was the first to be characterized by its generation in an argon matrix. [8] The interpretation of its infrared spectrum was greatly aided by MP2 calculations performed for o-benzyne and several of its isotopically labeled derivatives.…”

A Highly Efficient Triplet Analogue of a Thermal Biradical Cyclization—The Photochemical C2-C6 Cyclization of Enyne-Heteroallenes

“…[14] Herein, we now report for the first time on the photochemical reactions of enyne ± carbodiimides and enyne ± ketenimines constituting the first triplet analogues of a thermal biradical cyclization.…”

The Benzyne Story

“…The m-and p-benzynes 15 and 16, [8,19,55] tridehydrobenzenes 17-19, [19] and tetradehydrobenzenes (benzdiynes), e.g. 20 [20] (Scheme 10) are described herein.…”