Synthesis and some properties of 7h-naphth[3,2,1-cd]azulen-7-ones and related compounds
Journal of the Chemical Society. Perkin transactions 1 : organic and bio-organic chemistry Volume 2001
Page 1353-1358
published_at 2001
Title
Synthesis and some properties of 7h-naphth[3,2,1-cd]azulen-7-ones and related compounds
7H-Naphth[3,2,1-cd]azulen-7-ones are synthesized by the intramolecular Friedel-Crafts cyclization of diethyl 4-phenylazulene-1,3-dicarboxylate derivatives with polyphosphoric acid (PPA). Treatment of 7H-naphth[3,2,1-cd]azulen-7-one with methyl trifluoromethanesulfonate or perchloric acid gives 7-methoxynaphth[3,2,1-cd]azulenium trifluoromethanesulfonate or 7-hydroxynaphth[3,2,1-cd]azulenium perchlorate. Both spectroscopic inspection and molecular orbital calculations for 7-hydroxynaphth[3,2,1-cd]azulenium ion show that the tropylium moiety is a main contributor to the ground state in the resonance structure. The syntheses of 7H-azuleno[1,8-bc]phenanthren-7-ones and 5,7-dihydrodinaphth[3,2,1-cd:1,2,3-ij]azulene-5,7-diones are also described.
Languages
eng
Resource Type
journal article
Publishers
Royal Society of Chemistry
Date Issued
2001
File Version
Not Applicable (or Unknown)
Access Rights
metadata only access
Relations
[ISSN]0300-922X
[NCID]AA00695134
[isVersionOf]
[URI]http://www.rsc.org/Publishing/Journals/P1/