Mn(OAc)3-promoted sulfur-directed addition of an active methylene compound to alkenes

Various alkenes substituted at the 1,2-positions by phenyl, thiophene and furan rings were reacted with 3-(4-methoxyphenyl)-3-oxopropanenitrile in the presence of Mn(OAc)3·2H2O. The exact structure and configuration of the dihydrofuran derivatives formed were determined. In all cases only one regioi...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron 2012-07, Vol.68 (29), p.5838-5844
Main Authors: Deliomeroglu, Murat K., Dengiz, Cagatay, Çalışkan, Raşit, Balci, Metin
Format: Article
Language:English
Subjects:
Alkenes
Bonding
Chemistry
Cyclization
Derivatives
Dihydrofuran
Exact sciences and technology
Furan
Furans
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Manganese(III) acetate
Methylene
Organic chemistry
Phenyls
Preparations and properties
Tetrahedrons
Thiophene
Thiophenes
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Various alkenes substituted at the 1,2-positions by phenyl, thiophene and furan rings were reacted with 3-(4-methoxyphenyl)-3-oxopropanenitrile in the presence of Mn(OAc)3·2H2O. The exact structure and configuration of the dihydrofuran derivatives formed were determined. In all cases only one regioisomer was formed. The observed regioselectivity was explained on the basis of the formation of a complex between Mn(OAc)3, alkene, and 3-(4-methoxyphenyl)-3-oxopropanenitrile, which directs the mode of the addition to the double bond. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2012.05.003