A Novel 1,3-Stannyl Shift Promoted Intramolecular Cyclizations of α-Stannyl Radicals with a Formyl Group
Resource
Organic Letters 1 (6): 945-948
Journal
Organic Letters
Pages
945-948
Date Issued
1999
Date
1999
Author(s)
Chang, Sheng-Yueh
Shao, Yar-Fang
Chu, Shu-Fang
Fan, Gang-Ting
Tsai, Yeun-Min
Abstract
(equation presented) Reactions of α-stannyl bromides and xanthates with tributyltin hydride generate α-stannyl radicals. Intramolecular cyclizations of these radicals with a formyl group afford γ-stannyl alkoxy radicals that undergo a 1,3-stannyl shift from carbon to oxygen. The carbon radicals obtained can be trapped inter-or intramolécularly. Approximately, the rates of 5-exo cyclizations of α-stannyl radicals with a formyl group and terminal olefin are similar.
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Type
journal article
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