C6H4 Valence Bond Isomers:  A Reactive Bicyclopropenylidene

The simple bicyclopropenylidene derivative 21b, stabilized by fusion into naphthalene, results from reaction of dimesitylcyclopropenone 20b with the 1-trimethylsilyl-1H-cyclopropa[b]naphthalenyl anion. Although unstable in air, the molecule survives ambient conditions long enough for separation and...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2004-10, Vol.6 (22), p.4017-4020
Main Authors: Halton, Brian, Cooney, Mark J, Jones, Carissa S, Boese, Roland, Bläser, Dieter
Format: Article
Language:English
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The simple bicyclopropenylidene derivative 21b, stabilized by fusion into naphthalene, results from reaction of dimesitylcyclopropenone 20b with the 1-trimethylsilyl-1H-cyclopropa[b]naphthalenyl anion. Although unstable in air, the molecule survives ambient conditions long enough for separation and mass spectral characterization. Aerial oxidation of 21b leads to 2,3-dimesitylanthracene-1,4-dione 22b whose X-ray crystal structure has been determined. While diphenylcyclopropenone 20a does not give identifiable products, the di-tert-butyl analogue 20c gives quinone 22c but in lower yield.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol048307g