Synthesis and characterization of {2,6-bis[(dimethylamino)methyl]phenyl}tin(II) chloride and {2,6-bis[(dimethylamino)methyl]phenyl}(4-tolyl)tin(II), the first example of a mixed diaryltin(II) compound

Koten, G. van; Jastrzebski, J.T.B.H.; Schaaf, Paul A. van der; Boersma, J.; Zoutberg, Martin C.; Heijdenrijk, D.

doi:10.1021/om00107a038

Cited by 107 publications

(96 citation statements)

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“…These are similar to the Sn À N distances of 2.525 (8) and 2.602(8) reported for the heteroleptic organostannylene [{2,6-(Me 2 NCH 2 ) 2 C 6 H 3 }SnCl]. [16] Apparently, the Lewis acidity of the tin atoms in the latter compound and in compound 2 is rather similar.…”

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confidence: 82%

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Oxidation of Intramolecularly Coordinated Distannyne by S₈: From Tin(I) to Tin(IV) Polysulfide Via Tin(II) Sulfide

Bouška

Dostál

Růžička

et al. 2010

Chemistry A European J

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The investigation of heavier Group 14 element analogues of alkynes of the type (RE) 2 (where E = Si, Ge, Sn, or Pb) is of current interest. [1] These studies showed that the presence of rather bulky substituents such as a variety of substituted aryl and silyl groups allowed the synthesis of RE ER, which possess multiple bonds. [2] The studies dealing with the reactivity of the RE ER multiple bonds showed scission of the SiSi or GeGe triple bond by the addition of an olefin, [3] and most recently, Power and coworkers nicely outlined the cleavage of the Sn Sn multiple bond in the distannyne [ArSnSnAr] (Ar = C 6 H 3-2,6-(C 6 H 3-2,6-iPr 2) 2) by complexation with two molecules of either ethylene or norbornadiene. [4] Moreover, the latest study dealing with the reactivity of [ArSnSnAr] with cyclooctatetraene (cot) showed the powerful reducing character of the tin(I) compound towards neutral cot. [5] The reactivity studies of [ArSnSnAr] towards N 2 O also showed the reducing character of the Sn I species, yielding the organotin(II) oxide [Ar-SnOSnAr] as the final product. [6] Recently, the single-bonded dimeric species [{Si-A C H T U N G T R E N N U N G (NtBu) 2 CPh} 2 ] and [({2,6-(Me 2 NCH 2) 2 C 6 H 3 }Sn) 2 ] (1), as the first example of an SnÀN intramolecularly coordinated distannyne containing a built-in N,C,N-pincer-type ligand, were reported as well. [7] The redox reaction of [{SiA C H T U N G T R E N N U N G (NtBu) 2 CPh} 2 ] with N 2 O showed the reducing character of the Si I species, and led to the production of the well-defined [R 4 Si 4 O 6 ] com-[a] M.

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confidence: 82%

“…[16] The 1 H NMR spectrum showed the AX spin system at d A = 3.41 and d X = 3.80 ppm for the methylene groups CH 2 N and a singlet resonance at d = 2.35 ppm for the methyl NCH 3 groups, which is consistent with the molecular structure.…”

mentioning

confidence: 52%

Oxidation of Intramolecularly Coordinated Distannyne by S₈: From Tin(I) to Tin(IV) Polysulfide Via Tin(II) Sulfide

Bouška

Dostál

Růžička

et al. 2010

Chemistry A European J

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“…[14] The 119 Sn NMR spectrum revealed a resonance at d = 135.1 ppm that is shifted upfield when compared with heteroleptic organostannylene {2,6-(Me 2 NCH 2 ) 2 C 6 H 3 }SnCl (157 ppm). [15] Interestingly, the treatment of the latter compound with NaA C H T U N G T R E N N U N G (pyt) produced compound 2 in high yields as well (Scheme 3 in the Supporting Information).…”

Section: Ligand These Reactions Yielded Trans-[pt(me)a C H T U N G Tmentioning

confidence: 99%

Intramolecularly Coordinated [{2,6‐(Me₂NCH₂)₂C₆H₃}Sn^II]⁺: A Strong σ Donor for Pt^II

Martincová¹,

Dostál²,

Herres‐Pawlis³

et al. 2011

Chemistry A European J

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The reactivity of the late transition metals (TM) towards Sn II X 2 , where X is NR 2 , an organic group, or a halide, is still of current interest due to the fact that tin(II) dichloride is an important cocatalyst in various late-transition-metal-catalyzed reactions, such as hydrogenations, hydroformylations, or isomerization.[1] Most of these reactions show the general behavior of Sn II X 2 insertion into TM À Cl bonds and usually yield complexes with the general formula TMÀSnX 2 Cl with weakly coordinated Sn II anions, which have been postulated to have a strong trans-labilizing effect. [1][2][3] The exact role of Sn II X 2 as a cocatalyst is, however, still unclear. Better understanding of the nature of the interaction of the Sn II species with late transition metals was provided by Deelman and co-workers who studied the interaction of SnCl 2 and a Pt II complex in the presence of a catalytically relevant 2-PyPPh 2 ligand. These reactions yielded trans-II atom as a self-assembled P^Sn^P pincer ligand (Scheme 1).[4] The interaction of Sn II !Pt II was thus further supported by two head-to-head coordinated 2-PyPPh 2 ligands in bridging positions in complex I and the same group extended the nature of this motif to Sn II !Pd II interactions in a subsequent work.[5]In addition, recently Wagler et al. reported a structurally related metallastannatrane, [PdSnA C H T U N G T R E N N U N G (m-mt) 4 Cl 2 ], in which the Pd II !Sn IV interaction is supported by four mt ligands (mt = 1-methyl-2-mercaptoimidazolide) [6] and the same group extended the nature of this motif to Pd II !Si IV and Pt II !Si IV dative bonds (Scheme 1, II).[7] However, these metals!metallatranes contain inverse interactions between late transition metals and main-group metals, in which the transition metals act as s donors to the Lewis acidic center of the main-group elements.[8] Similar systems with various TM-E interactions (E = main-group element) were also reported by Bourrisou et al. [11]Armed with this knowledge together with the fact that we successfully synthesized several bimetallic complexes with Sn II !Pd II and Sn II !Pt II interactions, [12] we investigated the reactivity of the kinetically more robust complex cis-[Pt-A C H T U N G T R E N N U N G ({2,6-A C H T U N G T R E N N U N G (Me 2 NCH 2 ) 2 C 6 H 3 }SnCl) 2 Cl 2 ] (1, Scheme 2), with the N^C^N-chelating ligand 2,6-(Me 2 NCH 2 ) 2 C 6 H 3 À (hereafter denoted as L), [12c] towards the bridging mt ligand. However, the reaction of 1 with Na(mt) yielded only a complex mixture. On the other hand, reports dealing with the use of the pyridine-2-thionate (pyt) ligand (III, Scheme 1) in the Scheme 2. Synthesis of the mixture of complexes 2 and 3.

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“…Although this route to diorganotin dihalides is promising, a major disadvantage is that the number of stable divalent organotin compounds is very limited. However, we recently reported the synthesis and structural characterization of some novel homo- [16] and hetero-leptic diorganotin compounds [17] that could be expected to be converted into diorganotin dihalides by direct halogenation. We now report on the synthesis and structural characterization of some bis [8-…”

Section: Introductionmentioning

confidence: 99%

Oxidative-addition reactions of molecular diiodine and dibromine to divalent organotin compounds. Crystal structures of bis[8-(dimethylamino)-1-naphthyl]tin(IV) dibromide and {2,6-[bis(dimethylamino)methyl]phenyl}- (4-tolyl)tin(IV) diodide

Jastrzebski

Schaaf

Boersma

et al. 1991

Journal of Organometallic Chemistry

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Synthesis and characterization of {2,6-bis[(dimethylamino)methyl]phenyl}tin(II) chloride and {2,6-bis[(dimethylamino)methyl]phenyl}(4-tolyl)tin(II), the first example of a mixed diaryltin(II) compound

Cited by 107 publications

References 1 publication

Oxidation of Intramolecularly Coordinated Distannyne by S₈: From Tin(I) to Tin(IV) Polysulfide Via Tin(II) Sulfide

Oxidation of Intramolecularly Coordinated Distannyne by S₈: From Tin(I) to Tin(IV) Polysulfide Via Tin(II) Sulfide

Intramolecularly Coordinated [{2,6‐(Me₂NCH₂)₂C₆H₃}Sn^II]⁺: A Strong σ Donor for Pt^II

Oxidative-addition reactions of molecular diiodine and dibromine to divalent organotin compounds. Crystal structures of bis[8-(dimethylamino)-1-naphthyl]tin(IV) dibromide and {2,6-[bis(dimethylamino)methyl]phenyl}- (4-tolyl)tin(IV) diodide

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Synthesis and characterization of {2,6-bis[(dimethylamino)methyl]phenyl}tin(II) chloride and {2,6-bis[(dimethylamino)methyl]phenyl}(4-tolyl)tin(II), the first example of a mixed diaryltin(II) compound

Cited by 107 publications

References 1 publication

Oxidation of Intramolecularly Coordinated Distannyne by S8: From Tin(I) to Tin(IV) Polysulfide Via Tin(II) Sulfide

Oxidation of Intramolecularly Coordinated Distannyne by S8: From Tin(I) to Tin(IV) Polysulfide Via Tin(II) Sulfide

Intramolecularly Coordinated [{2,6‐(Me2NCH2)2C6H3}SnII]+: A Strong σ Donor for PtII

Oxidative-addition reactions of molecular diiodine and dibromine to divalent organotin compounds. Crystal structures of bis[8-(dimethylamino)-1-naphthyl]tin(IV) dibromide and {2,6-[bis(dimethylamino)methyl]phenyl}- (4-tolyl)tin(IV) diodide

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Oxidation of Intramolecularly Coordinated Distannyne by S₈: From Tin(I) to Tin(IV) Polysulfide Via Tin(II) Sulfide

Oxidation of Intramolecularly Coordinated Distannyne by S₈: From Tin(I) to Tin(IV) Polysulfide Via Tin(II) Sulfide

Intramolecularly Coordinated [{2,6‐(Me₂NCH₂)₂C₆H₃}Sn^II]⁺: A Strong σ Donor for Pt^II