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Metal Complexes of Cyanamides and their Alkylation to Cyanamidium Salts. A General Synthesis of Highly Substituted Ureas, Isoureas, and Guanidines
Author(s) -
Jochims Johannes C.,
AbuElHalawa Rajab,
Zsolnai Laszlo,
Huttner Gottfried
Publication year - 1984
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.19841170330
Subject(s) - chemistry , alkylation , primary (astronomy) , alkyl , metal , ammonia , lewis acids and bases , organic chemistry , medicinal chemistry , antimony , polymer chemistry , catalysis , physics , astronomy
The complexes 3a – p were prepared from disubstituted cyanamides and Lewis acids. According to a X‐ray structural analysis, the antimony pentachloride complex 3a is neither a s̀ nor a π complex (∡ CN – Sb 133°). The complexes 3 with SbCl 5 and FeCl 3 can be alkylated with tertiary alkyl chlorides, affording crystalline cyanamidium salts ( 5a – m ) which were characterized by reactions with water, primary or secondary alcohols to give ureas ( 11 ) and uronium salts ( 8a – z ), respectively. The guanidinium salts 9a – s were obtained with ammonia, primary and secondary amines.