Design of arylimine postmetallocene catalytic systems for olefin polymerization: I. Synthesis of substituted 2-cycloalkyl- and 2,6-dicycloalkylanilines

Oleinik, I. I.; Oleinik, I. V.; Абдрахманов, И. Б.; Ivanchev, S. S.; Толстиков, Г. А.

doi:10.1007/s11176-005-0025-4

Cited by 34 publications

(20 citation statements)

References 12 publications

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“…Generally for a given aniline, the condensation reaction occurs more readily for 2,6-pyridinedicarboxaldehyde than for 2,6-diacetylpyridine, while 2,6-dibenzoylpyridine is much less reactive under these conditions. Using this simple approach a wide variety of symmetrical examples of 1 have been prepared in which the steric bulk and electronic properties of the aryl groups have been systematically varied (see Tables 1 and 2 for complexed examples [1,2,3,4,5,6,7,8,9,10,11,12,13,14,15,17,20,21,24,26,27,29,28,32,33,36,37,38,39,40,41,42,44,48,18,16,19,22,23,25,30,31,34,35,45,43,46,…”

Section: Ligand Preparationmentioning

confidence: 99%

Iron-Based and Cobalt-Based Olefin Polymerisation Catalysts

Gibson¹,

Solan²

2008

Topics in Organometallic Chemistry

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This chapter describes the brief history of iron or cobalt catalysts for olefin polymerisation and oligomerisation. Since the discovery in 1998 that 2,6-bis(imino)pyridine iron and cobalt halides, on activation with MAO, can convert ethylene to highly linear polyethylene, numerous reports have been concerned with ligand modification, mechanisms for precatalyst activation, identifying the active species and understanding the mode of propagation/chain transfer. In addition, heterogenisation of this class of catalysts, their incorporation into macrocycles/ polymers and their use in reactor blending/tandem catalysis has seen some important developments; alternative ligand architectures that can support active iron and cobalt catalysts are also discussed as are different types of olefinic monomer.

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Section: Ligand Preparationmentioning

confidence: 99%

Iron-Based and Cobalt-Based Olefin Polymerisation Catalysts

Gibson¹,

Solan²

2008

Topics in Organometallic Chemistry

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“…2-Hydroxynaphthalene-1-carbaldehyde (I) and cycloalkylanilines II-IV were synthesized according to the procedures reported in [10,11].…”

Section: Methodsmentioning

confidence: 99%

10.1007/s11178-008-1012-0

2010

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Substituted o-cycloalkylanilines reacted with 2-hydroxynaphthalene-1-carbaldehyde in methanol in the presence of formic acid to give the corresponding Schiff bases as ligands for the synthesis of titanium(IV) complexes. * For communication VII, see [1].Matsui et al. [2] showed that titanium and zirconium chelates with salicylaldehyde imine ligands exhibit a high catalytic activity in polymerization of olefins and revealed a strong dependence of their catalytic activity on the structure of the aldehyde and amine fragments. Variation of substituents in the ligand could change the polymerization mechanism so that a broad spectrum of polyolefins with versatile parameters could be obtained [3]. It should be noted that ligands for the above complexes were synthesized mainly from substituted salicylaldehydes. Complexes with ligands based on naphthalenecarbaldehydes having a hydroxy group in the ortho position with respect to the aldehyde group were described in patent [4], but no data on their catalytic activity were given.While searching for new catalysts active at elevated temperature [5] we followed an approach based on introduction of a cycloalkyl group into the ortho position of an arene ring [6]. Such structural modification turned out to be successful for 2,6-bis(aryliminoalkyl)pyridine iron chloride complexes and 1,2-bis(arylimino)acenaphthene nickel bromide complexes. Catalysts on the basis of these complexes showed high efficiency over extended temperature range [7].In the present work we applied the above approach to the synthesis of Schiff bases from 2-hydroxynaphthalene-1-carbaldehyde and substituted anilines having a cyclopentyl, cyclohexyl, or cyclooctyl group in the ortho position with a view to make such compounds R = R′ = H (a), Me (c); R = Me, R′ = H (b); R = cyclo-C 4 H 7 (CH 2 ) n , R′ = H (d); II, V, n = 1; III, VI, n = 2; IV, VII, n = 4. CHO OH I + R NH 2 R' ( ) n IIa-IId, IIIa-IIId, IVa-IVc MeOH, HCOOH, 65°C OH N R' R ( ) n Va-Vd, VIa-VId, VIIa-VIIc Scheme 1.

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“…Anilines I3IV and 2,6-diacetylpyridine were synthesized by the procedures described in [1,9]. ³ J 1 8, J 2 3) ÄÄÄÄÄÁÄÄÄÄÄÄÄÄÄÄÄÁÄÄÄÄÄÄÄÄÄÄÄÄÄÄÄÄÄÄÄÄÄÄÄÄÄÄÄÄÄÄÄÄÄÄÄÄÄÄÄÄÄÄÄÄÄÄÄÄÄÄÄÄÄÄÄÄÄÄÄÄÄÄÄÄÄÄ 2,6-Bis[1-(2-R 1 -4-R 2 -6-cycloalkylphenylimino)ethyl]pyridines V3VIII (general procedure).…”

Section: Methodsmentioning

confidence: 99%

“…In the present work we extended these procedure to anilines containing cycloalkyl substituents with a view to obtain new 2,6-bis(aryliminoalkyl)pyridine structures V3VIII and optimized the reaction conditions. By reactions of 2-cyclopentyl-, 2,6-dicyclopentyl-(Ia3Ih), 2-cyclohexyl-, 2,6-dicyclohexyl (IIa3IId), 2cyclooctyl-(IIIa3IIIc), and 2-cyclododecylanilines (IVa3IVc) [1] with 2,6-diacetylpyridine on heating in an organic solvent in the presence of molecular sieves ÄÄÄÄÄÄÄÄÄÄÄÄ 1 For communicationh I, see [1]. catalyst; these conditions ensured 80385% yield of the target products.…”

mentioning

confidence: 99%