Direct Introduction of an N,N-Nonsubstituted Carboxamidine Group by Grignard Addition to Silylated Cyanamide

A new, widely applicable method to substitute a halogen atom by a nonsubstituted carboxamidine group is presented. Grignard addition to N , N -bis-trimethylsilylcarbodiimide gives amidinates, which split off the silyl groups during standard aqueous workup. The corresponding amidines are obtained in...

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Bibliographic Details
Published inSynlett Vol. 28; no. 12; pp. 1437 - 1440
Main Authors Guethner, Thomas, Huber, Eva, Sans, Juergen, Thalhammer, Franz
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 24.07.2017
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Grignard reactions
amidines
INSERTION
VERBINDUNGEN
MECHANISM
magnesium
CRYSTAL
CARBODIIMIDES
silylation
CHEMISTRY
carbodiimide
cyanamide
METAL-COMPLEXES
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Summary:A new, widely applicable method to substitute a halogen atom by a nonsubstituted carboxamidine group is presented. Grignard addition to N , N -bis-trimethylsilylcarbodiimide gives amidinates, which split off the silyl groups during standard aqueous workup. The corresponding amidines are obtained in high yield with high selectivity. Examples for purification procedures are given.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0036-1589000