Meta, para and meta, ortho double exo nucleophilic additions of trimethylsilylester enolates derived from saturated and unsaturated carboxylic acids to tricarbonylchromium complexes of aryl ethers: dearomatizing cyclization to lactones

Citation
H. Rudler et al., Meta, para and meta, ortho double exo nucleophilic additions of trimethylsilylester enolates derived from saturated and unsaturated carboxylic acids to tricarbonylchromium complexes of aryl ethers: dearomatizing cyclization to lactones, J ORGMET CH, 621(1-2), 2001, pp. 284-298
Citations number
41
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANOMETALLIC CHEMISTRY
ISSN journal
0022-328X → ACNP
Volume
621
Issue
1-2
Year of publication
2001
Pages
284 - 298
Database
ISI
SICI code
0022-328X(20010301)621:1-2<284:MPAMOD>2.0.ZU;2-N
Abstract
Potassium enolates derived from saturated and unsaturated bis(trimethylsily l) ketene acetals react with tricarbonylchromium complexes of anisole and d iphenylether to give, in addition to alpha -arylcarboxylic acids, the mono adducts, lactones, arising from a double exo nucleophilic addition. The lat ter were not observed in the case of benzenetricarbonylchromium. The interm ediate dienol ethers could be isolated and fully characterized by X-ray cry stallography. The influence of the nature of the substituents on the ketene acetals, of the nature of the oxidant, and of the nature of the ester enol ates on the course of the reaction has been established and will be discuss ed. (C) 2001 Elsevier Science B.V. All rights reserved.