2-Anilinomethyl

HFe3(CO)n]e [aus Fe3(CO)12 + II3C-OH in Benzol, Riickfl, 135 min]/Benzol Riickfl., 15 h 4-Anilinomethyl-benzoe- saure-methyleater 71 4-... 

Substitution of hydrogen by phenyl in the amide group changes the product composition considerably electrolysis of TV-phenyl-4-phenyl-4-pyridine carboxamide in 1 M hydrochloric acid at —0.75 V gives a mixture of 4-pyridinemethanol and 4-anilinomethyl-pyridine ... 

The extranuclear phthalazinethione, 4-benzyl-2-(5-thioxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)-l(2H)-phthalazinone (7, R = H) underwent regular 5-aIkyla-tion to give, for example, 4-benzyl-2-(5-methylthio-l,3,4-oxadiazol-2-yl)-l(2H)-phthalazinone (8) but Mannich A-(aminoalkylation) to give, for example, 4-benzyl-2-(4-anilinomethyl-5-thioxo-4,5-dihydro-l,3,4-oxadiazol-... 

It has been suggested that the amine radical cation (46) is not directly involved in initiating chains and that most polymerization is initiated by benzoyloxy radicals.179 However, Sato et a ." employed spin trapping (3.5.2.1) to demonstrate that the anilinomethyl radical (45) was formed from the radical cation (46) by loss of a proton and proposed that the radical 45 also initiates polymerization. Overall efficiencies for initiation by amine-peroxide redox... 

In wafir. Athanol mit Acetatpuffer erhalt man dagegen aus 2-Aminocarbonyl- bzw. in 1 n Salzsaure aus 2-(N-Methyl-anilinocarbonyl)-l,3-thiazol 2-Hydroxymethyl-l,3-thiazol (59 bzw. 67% d.Th.). 2-Anilinomethyl-1,3-thiaz.ol (50% d.Th.) wird aus dem Anilid in 0,8 n Salzsaure bei —0.7 V gebildet7. 

N-(4-Chlor-anilinomethyl)- 453 N-(4-Cyan-anilinomethy )- 453 N-(N, 4-Dimethyl-anilinomethyl)- 254 N-Diphcnylmethyl- 255 3 -Hydroxy-N -propyl - 257 N-Methyl-3-benzyl-2-benzyliden- 581 N-Methyl-bis-fbenzylidenJ- 581 N-Methyl-2,3-dibenzyl- 581 N-Phcnyl- 256 N-Pyrrolidinomethyl- 452... 

Methyl-2-(4-brom-N-methyl-anilinomethyl)- 661 Bicyclo[3.3.1 ]nonan... 

Almost diastereomerically pure (2i ,55)-l,3-diaza-2-methoxy-3-alkyl-2-phosphabicyclo[3.3.0]octanes (201a-d) were formed in the reaction of (S)-2-anilinomethyl)-pyrrolidines (197b-e) with methyl dichlorophosphite in the presence of NEt3 (Scheme 55) [86], With these ligands, high stereoselectivity (ee s up to 91%) was observed in the Pd catalyzed ally lie animation reaction [86],... 

Diastereomerically pure (2W,5.V)-l,3-diaza-2-(2-methylphenyl)-3-phenyl-2-phosphabicyclo[3.3.0]octane (.S )-202] was formed in the thermal reaction of (S)-2-(anilinomethyl)pyrrolidines (197a) with o-TolP(NMe2)2 and isolated in 27% yield after recrystallization (Scheme 56) [87], Its cyclopalladation with palladium diacetate followed by anion metathesis gave dimer (5,5)-203 (Scheme 56) [87],... 

A highly diastereoselective exchange reaction between a variety of bis(dimethy-lamino)arylphosphines and (S)-2-(anilinomethyl)pyrrolidine (197a) and its SV-aryl analogues constituted a key step in the synthesis of a series of substituted monodonor diazaphospholidine ligands, 213-220 [90, 91] (Figure 1). 

However, compound 57, containing two 1,3-azaphosphetidine fragments, obtained by heating tetrakis(aminomethyl)phosphonium (38) chloride or tris(anilinomethyl)phosphine (40) in ethanol, is described in Eq. (28) (72JOC2752 77JOC4040). A detailed analysis of NMR spectra made it possible to reject a structure with two five-membered rings. 

Anilinomethyl-glucoimidazole (129) (5tf,6/ ,7S,SS)-5-(Hydroxymethyl)-2-(phenylamino)methyl-5,6,7,8 -tetrahydro-imidazo [ 1,2-a] pyridine- 6,7,8-triol... 

When the ketone (65) was treated with the chiral reagent produced by decomposing LiAlH with (S)-2-(anilinomethyl) pyrrolidine, the alcohol (66) obtained in 60 % yield. The optical yield could be determined as 62 % e.e. 95). 

The diamine (99) was prepared from (S)-proline90b) or (S)-glutamic acid I15) maintaining the asymmetric center. Racemic 2-(anilinomethyl)pyrrolidine, prepared from (RS)-5-oxopyrrolidine-2-carboxylic acid, was effectively resolved into a pair of enantiomers by fractional crystallization of its mandelic acid salt U6). Moreover, the preferential crystallization of its 4-hydrobenzoic acid salt was found to produce both enantiomers in high optical purities by alternate seeding116). 

Asymmetric Michael addition. This pyrrolidine is an efficient catalyst for asymmetric Michael addition of thiols to cyclohexenone (cf. 8, 431). (S)-2-(Anilinomethyl)-1-ethylpyrrolidine, which lacks the 4-hydroxyl group of 1, has little effect on enantioselection. The important role of a hydroxyl group in several asymmetric inductions has already been noted. 

Asymmetric reduction of ketonesLithium aluminium hydride in conjunction with this chiral ligand reduces prochiral aromatic ketones to (S)-secondary alcohols in 90-95% optical yields. Optical yields are lower (10-40% ee) in the case of alkyl aryl ketones. It is superior to (S)-2-(anilinomethyl)pyrrolidine for this reduction. Evidently the two methyl groups enhance the enantioselectivity. 

ASYMMETRIC MICHAEL ADDITIONS (2S,4S)-(Anilinomethyl)-l-cthyl-4-hydroxy-pyrrolidinc. 

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