A Novel 1,3-Stannyl Shift Promoted Intramolecular Cyclizations of α-Stannyl Radicals with a Formyl Group | Zendy

ShengYueh Chang | Zendy; YarFang Shao | Zendy; ShuFang Chu | Zendy; GangTing Fan | Zendy; YeunMin Tsai | Zendy

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A Novel 1,3-Stannyl Shift Promoted Intramolecular Cyclizations of α-Stannyl Radicals with a Formyl Group

Author(s) -

ShengYueh Chang,

YarFang Shao,

ShuFang Chu,

GangTing Fan,

YeunMin Tsai

Publication year - 1999

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol990199o

Subject(s) - chemistry , radical , tributyltin hydride , intramolecular force , olefin fiber , alkoxy group , medicinal chemistry , tributyltin , hydride , stereochemistry , carbon atom , photochemistry , organic chemistry , catalysis , ring (chemistry) , hydrogen , alkyl

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 intramolecularly. Approximately, the rates of 5-exo cyclizations of α-stannyl radicals with a formyl group and terminal olefin are similar.

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