New camphor derivatives functionalized at C-3 and C-10

Authors
Vostrikov, NS Abutkov, AV Miftakhov, MS
Citation
Ns. Vostrikov et al., New camphor derivatives functionalized at C-3 and C-10, RUSS J ORG, 37(1), 2001, pp. 20-22
Citations number
13
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
10704280 → ACNP
Volume
37
Issue
1
Year of publication
2001
Pages
20 - 22
Database
ISI
SICI code
1070-4280(200101)37:1<20:NCDFAC>2.0.ZU;2-2
Abstract
Base-catalyzed condensation of 10-methylenecamphor with diethyl oxalate gav e the corresponding (Z)-3-ethoxycarbonyl(hydroxy)methylene derivative which was converted into methyl ether and acetate. The Z-methyl ether undergoes isomerization into the E-methyl ether on treatment with N-bromosuccinimide in the presence of radical initiator [azobis(isobutyrodinitrile)]. (Z)-3-Et hoxycarbonyl(hydroxy)methylene-10-methylenecamphor smoothly reacts with N-b romosuccinimide to afford stereoisomeric 3-bromo derivatives.