Konjugation in makrocyclischen Bindungssystemen, XXXI. Isomere Naphtho[14]annulene mit 1,2- und 2,3-Anellierung
Zur Synthese von Naphtho[1,2-α][14]annulen (1) und Naphtho[2,3-α][14]annulene (2) wurden die 1,2- und 2,3-Di(1-hexen-5-inyl)naphthaline 4 und 8 dargestellt. Cyclisierung von 4 und 8 durch oxidative Kupplung ergab 5 bzw. 9, deren prototrope Isomerisierung zu 1 bzw. 2 dagegen die symmetrische Struktur 2A. 1B zeigt masig starke Diatropie im [14]Annulen-System, wahrend fur 2A keine Diatropie nachzuweisen ist. 
 
 
 
Conjugation in Macrocyclic Systems, XXXI. – Isomeric Naphtho[14]annulenes with 1,2- and 2,3-Annellation 
 
 
 
For the syntheses of naphtho[1,2-α][14]annulene (1) and naphtho[2,3-α][14]annulene (2) the 1,2- and 2,3-di(1-hexen-5-ynyl)naphthalenes 4 and 8, respectively, were prepared. Cyclisation of 4 and 8 by oxidative coupling yielded 5 and 9, respectively, the prototropic isomerisation of which led to 1 and 2, respectively. – On the basis of 1H NMR spectra structure 1B was assigned to 1 whereas the different annellation type 2A was proven for 2. 1B shows fairly strong diatropicity in the [14]annulene system; no evidence for diatropicity was found, however, for the 2,3-annellated isomer 2A.