137594-16-2Relevant articles and documents
On the Reaction of (Vinylimino)phosphoranes and Related Compounds. 20. Syntheses and Properties of Methanocyclodecapyridine Ring Systems
Kanomata, Nobuhiro,Kawaji, Hiroyuki,Nitta, Makoto
, p. 618 - 625 (2007/10/02)
Novel 2--1,6-methanoannulenes (8x, y) and 3--1,6-methanolannulenes (9x, y) were generated by the Staudinger reaction of 2- and 3-azido-1,6-methanoannulenes (5 and 6).The compound 8x was inert to α,β-unsaturated ketones, while compounds 8y adn 9y were found to react with α,β-unsaturated ketones in enamine-alkylation process followed by aza-Wittig reaction and dehydrogenation to give 7,12- and 5,10-methanocyclodecapyridines 20a-f and 26a, f, respectively.The reactivity of 8 and 9 as well as the site selectivity of 9 was suggested by their 13C NMR spectra, in which the carbon signals of the nucleophilic center appear at higher field as compared to those of 1,6-methanoannulene.Structural properties of 20a-f and 26a, f were remarkable reduction of a ring current and appearance of bond alternation as compared to the parent 1,6-methanoannulene (1).The UV spectra exhibiting a prolonged cyclic conjugation are in contrast to their 10? electron analogues, 1,6-methanoannulene (1) and quinoline derivatives.