Metallierung und C-C-Kupplung von 2-Pyridylmethylamin: Synthese und Strukturen von Methylzink-2-pyridylmethylamid, Tris(trimethylsilyl)methylzink-2-pyridylmethylamid und (Z)-1-Amino-1,2-bis(2-pyridyl)ethen

Westerhausen, Matthias; Bollwein, Tobias; Mayer, Péter; Piotrowski, Holger; Pfitzner, Arno

doi:10.1002/1521-3749(200206)628:6<1425::aid-zaac1425>3.0.co;2-7

Cited by 32 publications

(20 citation statements)

References 22 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The alkylzinc amide compounds 210 289 , 211 290 and 212 291 , derived from the corresponding 2-(aminomethyl)pyridines, have structural features identical to those of 203-208 ( Figure 100). They form dimers in which the amide nitrogen atom is µ 2 -bridged between The structure of dimer 218 is remarkable (Figure 101) 78 .…”

Section: T-bu T-bu T-bu T-bu T-bu T-bumentioning

confidence: 98%

Structural Organozinc Chemistry

Jastrzebski¹,

Boersma²,

Koten³

2006

The Chemistry of Organozinc Compounds

View full text Add to dashboard Cite

Section: T-bu T-bu T-bu T-bu T-bu T-bumentioning

confidence: 98%

Structural Organozinc Chemistry

Jastrzebski¹,

Boersma²,

Koten³

2006

The Chemistry of Organozinc Compounds

View full text Add to dashboard Cite

“…The oxidative C-C coupling of 2-pyridylmethylamine also led to the formation of various byproducts [18]. Protection of the amino functionalities by trialkylsilyl groups led to a quantitative formation of the C-C coupled product [di(methylzinc) 1,2-di(2-pyridyl)-1,2-bis(trialkylsilylamido)ethane] G, as shown in Eq.…”

Section: Introductionmentioning

confidence: 98%

Synthesis of 1,4-Diamino-2,3-di(2-pyridyl)butane and its Dinuclear Zinc(II) Chloride Complex

Kloubert

Schulz

Görls

et al. 2009

Zeitschrift Für Naturforschung B

Self Cite

View full text Add to dashboard Cite

In a Henry-type reaction nitromethane reacts with N-(2-pyridylmethylidene)-methylamine (1) yielding 1-methylamino-1-(2-pyridyl)-2-nitromethane (2) in nearly quantitative yield. This orange compound decomposes slowly in an inert gas atmosphere and fast in contact with air. Therefore 2 has to be stored at −78 • C as a methanol solution. Reduction of 2 with hydrogen in the presence of a Pd/C catalyst leads to the formation of 1,4-dinitro-2,3-di(2-pyridyl)butane (3) in the rather poor yield of 12 %. The major product is the meso-isomer, meso-3, whereas only traces of (R, R)-and (S, S)-isomers of 3 are formed. A conversion of the nitro groups into amino functionalities succeeds with hydrazine hydrate in the presence of a Pd/C catalyst yielding meso-1,4-diamino-2,3-di(2-pyridyl)butane (4). Recrystallization from an aqueous solution gives 4·2H 2 O. The zinc(II) chloride complex 5 with the metal atoms in distorted tetrahedral environments can be isolated after addition of two equivalents of ZnCl 2 to 4. The molecular structures of trimeric 1, meso-3, (R, R)/(S, S)-3, meso-4, and 5 have been determined and are discussed.

show abstract

“…In recent years our group has studied their reaction behavior towards dialkylzinc compounds in order to obtain multinuclear zinc complexes. amine reacts with dialkylzinc to form the corresponding alkylzinc (2-pyridylmethyl)amide which, depending on the size of the zinc bound alkyl substituent, crystallizes either as dimer or trimer [5]. Zincation of N-silylated (2-pyridylmethyl)amine (I) with alkylzinc reagents yields the dimeric silylamide (III).…”

Section: Introductionmentioning

confidence: 99%