
%0 Journal Article
%A Jessup, PJ 
%A Reiss, JA 
%T Cyclophanes. VII. Naphthalene and phenanthrene cyclophanes for the synthesis of coronene
%J Australian Journal of Chemistry
%D 1977/04/01
%V 30
%N 4
%P 843-850
%K 
%R https://doi.org/10.1071/CH9770843
%U https://www.publish.csiro.au/paper/CH9770843 
%X A coupling reaction between 3,6-bis(bromomethyl)phenanthrene and p- xylene-&#945;,&#945;?-dithiol gave 2,11-dithia[3,3](3,6)phenanthroparacyclophane (4). Ring-contraction of the sulphonium salt (5)proceeded in low yield. However, a corresponding dimethyl cyclophane (12) reacted efficiently togive the desired ring-contracted [2,2]cyclophane (13). Wittig rearrangement of the cyclophane (4) gave a high yield of compound (7) which in turn was oxidized to the disulphoxide (8). Thermal elimination of methylsulphenic acid produced the diene (9) which could be photochemically cyclized to coronene. A similar series of reactions with 2,13-dithia[3,3](2,7)naphthalenophane (14) was effected. Oxidation, halogenation and photochemical reactions of both the naphthalene- and phenanthrene-based cyclophanes are reported. 
