Reductive cleavage of benzannelated cyclic ethers and amines: Synthetic applications

Authors
Azzena, U Demartis, S Pilo, L Piras, E
Citation
U. Azzena et al., Reductive cleavage of benzannelated cyclic ethers and amines: Synthetic applications, TETRAHEDRON, 56(42), 2000, pp. 8375-8382
Citations number
27
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
56
Issue
42
Year of publication
2000
Pages
8375 - 8382
Database
ISI
SICI code
0040-4020(20001013)56:42<8375:RCOBCE>2.0.ZU;2-T
Abstract
Reduction of symmetrical intramolecular diarylmethyl ethers (3a and 8a) and amines (3b and 8b) with alkali metals in THF allows the generation of unsy mmetrical oxy- or amino-functionalised arylmethyl organometallics. Such int ermediates were successfully trapped with various electrophiles, allowing a new access to unsymmetrically 2,2'-disubstituted-1,1'-biaryls (5aa-5bf) an d 1,8-disubstituted naphthalenes (10aa-10be). (C) 2000 Elsevier Science Ltd . All rights reserved.