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Unusual Reaction of 1,1‐Dilithio‐2,3,4,5‐tetraphenylsilole with 1,3‐Dienes Yielding Spirosilanes and Elemental Lithium
Author(s) -
Toulokhonova Irina S.,
Friedrichsen Dennis R.,
Hill Nicholas J.,
Müller Thomas,
West Robert
Publication year - 2006
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200503362
Subject(s) - lithium (medication) , adduct , chemistry , yield (engineering) , ion , lithium metal , inorganic chemistry , medicinal chemistry , organic chemistry , materials science , metallurgy , electrode , electrolyte , medicine , endocrinology
Reducing the reluctant : 1,1‐dilithiosilole 1 reacts with 1,3‐dienes and undergoes an unusual “oxidative cyclization”, in which lithium ions are reduced to metallic lithium and spirosilole adducts like 2 (see scheme) are formed in high yield. This transformation proceeds through well‐ordered transition‐state geometries, in which the lithium ions play a decisive role.