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{6 Lithio(trimethylsilyl)diazomethane· 2 Lithio[4,5‐bis(trimethylsilyl)triazene]· 7 Diethyl Ether}: The First X‐Ray Structure Analysis of a Lithiated Diazoalkane
Author(s) -
Boche Gernot,
Harms Klaus,
Marsch Michael,
Schubert Frank
Publication year - 1994
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.1491271118
Subject(s) - diazomethane , chemistry , trimethylsilyl , deprotonation , ether , triazene , medicinal chemistry , methyllithium , diethyl ether , protonation , organic chemistry , ion
The crystals of {6 lithio(trimethylsilyl)diazomethane· 2 lithio[4,5‐bis(trimethylsilyl)triazene]· 7 diethyl ether} provide for the first time insight into the structure of a lithiated diazomethane, namely that of lithiated (trimethylsilyl)diazomethane ( 11c ). Furthermore, the crystals contain lithiated 4,5‐bis‐(trimethylsilyl)triazene ( 12 ), a reaction product of (trimethylsilyl)diazomethane and its Li compound 11c which is analogously found in deprotonation/protonation reactions of other monosubstituted diazomethanes. This structure, together with quantum chemical calculations, leads to a better understanding of the so far rather complex chemistry of lithiated (monosubstituted) diazoalkanes.