synthesis and reactions of dibenzo[a,e]pentalenes的合成和反应指pentalenes(a,e).pdfVIP

Symmetry 2010, 2, 950-969; doi:10.3390/sym2020950 OPEN ACCESS symmetry ISSN 2073-8994 /journal/symmetry Review Synthesis and Reactions of Dibenzo[a,e]pentalenes Masaichi Saito * Department of Chemistry, Graduate School of Science and Engineering, Saitama University, Shimo-okubo, Sakura-ku, Saitama-city, Saitama 338-8570, Japan; E-Mail: masaichi@chem.saitama-u.ac.jp Received: 28 January 2010; in revised form: 11 March 2010 / Accepted: 20 April 2010 / Published: 21 April 2010 Abstract: Pentalene has recently received a considerable amount of attention as a ligand in sandwich-type transition metal complexes. In contrast, dibenzo[a,e]pentalene (hereafter denoted as dibenzopentalene), which is more -extended than pentalene, has received less attention, despite its potential usefulness as a building block of ladder-type -conjugated molecules, which have recently received growing interest. However, very recently, several novel efficient methods for the synthesis of dibenzopentalenes have been reported. This review surveys recent advances in the synthesis and reactions of dibenzopentalenes and describes the aromaticity of their ionic species. Keywords: dibenzopentalene; thermolysis; skeletal rearrangement; reductive cyclization; catalyst; redox reaction 1. Introduction The parent pentalene has 8 electrons, which indicates its antiaromatic nature, and is very highly reactive, having only been observed using a matrix isolation technique at 196 °C (Chart 1) [