Thallium trinitrate-mediated ring contraction of 1,2-dihydronaphthalenes: an approach to the synthesis of indans

Authors
Ferraz, HMC Silva, LF Vieira, TO
Citation
Hmc. Ferraz et al., Thallium trinitrate-mediated ring contraction of 1,2-dihydronaphthalenes: an approach to the synthesis of indans, TETRAHEDRON, 57(9), 2001, pp. 1709-1713
Citations number
31
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
57
Issue
9
Year of publication
2001
Pages
1709 - 1713
Database
ISI
SICI code
0040-4020(20010225)57:9<1709:TTRCO1>2.0.ZU;2-6
Abstract
Oxidation of 1,2-dihydronaphthalenes with thallium trinitrate was studied. 1,2-dihydronaphthalene, 1-methyl-1,2-dihydronaphthalene, 6- and 8-methoxy-1 ,2-dihydronaphthalenes gave rise to the respective ring contraction product s in good yields, whereas the rearrangement was not observed using 4-methyl -1,2-dihydronaphthalene and 1-n-butyl-4-methyl-1,2-dihydronaphthalene as su bstrates. (C) 2001 Elsevier Science Ltd. All rights reserved.