Title of article
Regiochemical control in intramolecular cyclizations of 2,3-epoxysulfides mediated by solvent effects
Author/Authors
Sivakumar ، نويسنده , , Meenakshi and Borhan، نويسنده , , Babak، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2003
Pages
5
From page
5547
To page
5551
Abstract
The regioselectivity of cyclization in methylene-interrupted epoxydiols with a thiophenyl ether group adjacent to the epoxide can be controlled by the appropriate choice of reaction conditions. Thus, while the 5-exo mode of cyclization is observed under protic conditions with polar solvents, the intermediacy of an episulfonium ion generated in non-polar solvents lead to a regioisomeric THF product.
Keywords
tetrahydrofuran rings , epoxysulfides , episulfonium , regiochemical control , Epoxide opening
Journal title
Tetrahedron Letters
Serial Year
2003
Journal title
Tetrahedron Letters
Record number
1653591
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