Synthesis and Crystal Structure of Dimorphic Dibenzo[cde,opq]rubicene

Abstract

Dibenzo[cde,opq]rubicene has been synthesized by an eight‐step reaction sequence including an iron‐mediated [2+2+1] cycloaddition and a flash vacuum pyrolysis as key steps. Two crystal modifications of the S‐shaped, planar polycyclic aromatic hydrocarbon have been obtained and characterized by X‐ray diffractometry.

Halo-Jacobsen Rearrangement Induced by Steric Repulsion between peri-Iodo Groups

“…1,8-Diidonaphthalene 1 and the comparison, 1,5-diidonaphthalene 2, were synthesized from commercially available diaminonaphthalenes by diazotization followed by Sandmeyer reaction. 10 Since the crystallographic data of 1 and 2 were already provided, 7,11 we compared their structural parameters (Table 1). The crystal system of 1 contains six independent molecules in a unit cell, and structural parameters were varied.…”

Copper-catalyzed nitration of electron-deficient BN-naphthalene

“…In fact, its pinpoint synthesis constituted a multistep sequence of dinitration, reduction and Sandmeyer reaction to deliver the final product of 1,8-diiodonaphthalene. 19,20 This existing multistep approach is limited in scope and mired by the use of hazardous and strong oxidizing acids as well as poor selectivity issues, so is less likely to serve as a model for the synthesis of sensitive BN-heteroaromatics (Fig. 1).…”