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Siloxymethylamines as Aminomethylation Reagents for Amines Leading to Labile Diaminomethanes That can be Trapped as Their [Mo(CO) 4 ] Complexes
Author(s) -
Sharma Hemant K.,
Gonzalez Paulina E.,
Craig Alexander L.,
Chakrabarty Sanchita,
MettaMagaña Alejandro,
Pannell Keith H.
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201600810
Subject(s) - disproportionation , chemistry , denticity , reagent , metal , medicinal chemistry , stereochemistry , diamine , crystallography , crystal structure , catalysis , polymer chemistry , organic chemistry
Compound Et 3 SiOCH 2 NMe 2 transfers Me 2 NCH 2 to R 2 NH (R 2 =Et 2 , PhMe, [Cr(η 6 ‐C 6 H 5 )(CO) 3 ]Me, PhH) to form previously unknown diaminomethanes, Me 2 NCH 2 NR 2 and, in the case of R 2 =PhH, the triamine Me 2 NCH 2 N(Ph)CH 2 NMe 2 . The diaminomethanes exhibit an unreported disproportionation to a mixture of (R 2 N) 2 CH 2 , (Me 2 N) 2 CH 2 , and Me 2 NCH 2 NR 2 , which can be trapped as their [Mo(CO) 4 (diamine)] complexes. Whereas PhMeNCH 2 NMe 2 is a labile material, the metal‐substituted ([(η 6 ‐C 6 H 5 )Cr(CO) 3 ]MeNCH 2 NMe 2 is a stable material. The triamine Me 2 NCH 2 N(Ph)CH 2 NMe 2 is unstable with respect to transformation to 1,3,5‐triphenyltriazine, but is readily trapped as the bidentate‐triamineMo(CO) 4 . All metal complexes were characterized by single‐crystal X‐ray diffraction.