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Elemento‐Organic Amines and Imines
Author(s) -
Scherer O. J.
Publication year - 1969
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.196908611
Subject(s) - chemistry , imine , amine gas treating , nitrogen , sulfur , ligand (biochemistry) , chloride , medicinal chemistry , main group element , phosphorus , bond cleavage , polymer chemistry , stereochemistry , organic chemistry , catalysis , transition metal , biochemistry , receptor
Amines with mixed substituents containing two or three ElN bonds El = a higher IVa, Va, or VIa element; by IVa, Va, and VIa elements are meant elements of the IV, V, and VI main groups of the periodic system . are relatively stable if one or two of these bonds are (CH 3 ) 3 SiN bonds. IR and 1 HNMR studies indicate that the (p → d)π bond components of the element‐nitrogen bonds steadily decrease from silicon, phosphorus, and sulfur toward their higher homologs. Because of the differences in the polarities of the element‐nitrogen bonds, these substances can be used for selective insertion and cleavage reactions. The reaction of metalated N‐silylaminoarsines with methyl chloride as well as the reaction of metalated N‐trimethyl(IVa)‐element‐substituted amino‐tert‐butylphosphines with halogenotrimethyl(IVa) element compounds open new, simple routes for the conversion of elemento‐organic amine systems into imine systems. The problem of reversible and irreversible (CH 3 ) 3 El ligand migration (1,3 shift) is discussed for trimethyl(IVa)element‐substitued benzamidines, diaminophosphines, aminoiminophosphoranes, sulfinamides, and aminosulfimines.