Magnetic double resonance studies of 119Sn chemical shifts in organotin compounds

Davies, Alwyn G.; Harrison, P. G.; Kennedy, John D.; Mitchell, Terence N.; Puddephatt, Richard J.; McFarlane, William

doi:10.1039/j39690001136

Cited by 75 publications

(23 citation statements)

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“…11 It was therefore of interest to study the 119 tin chemical shifts of the allyltin trichlorides generated by transmetallation of the alkoxypent-2-enylstannanes to see whether they were consistent with co-ordination of the tin by the alkoxy groups. 12,13 Transmetallation of prop-2-enyl(tributyl)-and -(triphenyl)-stannanes 56 and 59 gave prop-2-enyltin trichloride 57 and either tributyltin chloride 58 or triphenyltin chloride 60 with 119 Sn chemical shifts similar to those in the literature, 12,14,15 see Fig. 5.…”

Section: Resultssupporting

confidence: 71%

Concerning the 1,5-stereocontrol in tin(iv) chloride promoted reactions of 4- and 5-alkoxyalk-2-enylstannanes: trapping intermediate allyltin trichlorides using phenyllithium

Hobson

Thomas

2012

Org. Biomol. Chem.

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Transmetallation of the 5-benzyloxy-4-methylpent-2-en-1-yl(tributyl)- and -(triphenyl)stannanes 1 and 8 using tin(iv) chloride generates an allyltin trichloride that reacts with aldehydes to give (Z)-1,5-anti-6-benzyloxy-5-methylhex-3-en-1-ols 2. The allyltin trichloride believed to be the key intermediate in these reactions has been trapped by phenyllithium to give anti-5-benzyloxy-4-methylpent-1-en-3-yl(triphenyl)stannane 9. Transmetallation of this anti-5-benzyloxy-4-methylpent-1-en-3-yl(triphenyl)stannane 9 generated an allyltin trichloride that reacted with aldehydes to give the (Z)-1,5-syn-6-benzyloxy-5-methylhex-3-en-1-ols 23 and was trapped by phenyllithium to give syn-5-benzyloxy-4-methylpent-1-en-3-yl(triphenyl)stannane 24. Similar stereoselectivity was observed for tin(iv) chloride promoted reactions of this syn-5-benzyloxy-4-methylpent-1-en-3-yl(triphenyl)stannane 24 with aldehydes and with phenyllithium. The allyltin trichlorides generated by transmetallation of 4-hydroxy- and 4-benzyloxy-pent-2-enyl(triphenyl)stannanes 34 and 35 were similarly trapped by phenyllithium to give 4-hydroxy- and 4-benzyloxy-pent-1-en-3-ylstannanes 36 and 37 whose configurations were established by correlation with known compounds. This work confirmed the configurations of the intermediate allyltin trichlorides involved in tin(iv) chloride promoted reactions of 4- and 5-alkoxypent-2-enylstannanes with aldehydes and showed that the high levels of remote stereocontrol were due mainly to kinetically controlled transmetallation. A fuller mechanistic scheme is proposed for the reactions in the 5-benzyloxy-4-methylpent-2-enylstannane series together with relevant (119)Sn NMR data.

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Section: Resultssupporting

confidence: 71%

Concerning the 1,5-stereocontrol in tin(iv) chloride promoted reactions of 4- and 5-alkoxyalk-2-enylstannanes: trapping intermediate allyltin trichlorides using phenyllithium

Hobson

Thomas

2012

Org. Biomol. Chem.

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“…Values [23,24] for similar five and six coordinated Bu 2 Sn(IV) complexes have been reported in the range of δ -128 to -165 ppm and ~ δ -365 ppm, respectively. Values [23,24] for similar five and six coordinated Bu 2 Sn(IV) complexes have been reported in the range of δ -128 to -165 ppm and ~ δ -365 ppm, respectively.…”

Section: Sη Nmr Spectramentioning

confidence: 55%

Spectral and Antimicrobial Studies of Organotin(iv) Complexes of Bidentate Schiff Bases Having Nitrogen and Sulphur Donor Systems

Singh¹,

Khungar²,

Tripaathi³

et al. 2001

Main Group Metal Chemistry

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The complexes of composition R 2 Sn(L)2 and RjSnL (where R = butyl and L = monoanion of Schiff bases of S-benzyldithiocarbazate) have been prepared by the reaction of Schiff bases with metal oxides. The newly synthesized complexes have been characterized by elemental analysis, conductance measurements and molecular weight determinations. The mode of bonding and geometry of the complexes have been suggested on the basis of IR, UV and multinuclear 'H, i3 C and Sn NMR spectral studies. Schiff bases and their tin complexes have also been screened for their antibacterial activities, as several bacteria are quite active in this respect. Preparation of S-benzyldithiocarbazateThis compound was prepared by the method of Bähr and Schleitzer[8], Since their details are rather brief and conditions for a high yield are critical, the method is given here in detail. Potassium hydroxide (28.5 g) was completely dissolved in alcohol (135 ml)-water (15 ml) mixture and the mixture was cooled in ice. To the solution hydrazine hydrate (25 g) was added slowly with stirring. A solution of carbon disulphide (36.5 g) in alcohol (30 ml) was then added dropwise from a burette, with constant stirring, over a period of Ihr. The temperature of the mixture was kept below 10 °C during the addition. The resulting yellow oil was separated by means of a separatory funnel and dissolved in alcohol (48 ml)-water (72 ml) mixture and this solution was cooled in ice. Benzyl chloride (62.16 g) was then added slowly with vigorous mechanical stirring; after the addition the mixture was stirred for a further 10 minutes while a white product separated. Ice-cooled water (100 ml) was and then added the stirring was continued for another 10 minutes. 5Brought to you by | Purdue University Libraries

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“…14c,d The individual interactions are not important; but they are essential to the supramolecular structure, so they manage the growing of the crystal packing, Figure 4. C11 C10 Sn1 120.4(3) O2 Sn1 C16 92.31(11) C12 C13 1.380 (11) C15 C10 Sn1 121.4(3) C13 C14 1.335 (11) C10 C11 C12 120.8(6) C14 C15 1.388(6) C11 C12 C13 119.2(6) C16 C17 1.374(5) C12 C13 C14 120.8(5) C16 C21 1.380 (5) C13 C14 C15 120.0(6) C16 Sn1 2.124(3) C14 C15 C10 121.1(5) C17 C18 1.386(6) C17 C16 C21 117.9(3) C18 C19 1.353 (7) C17 C16 Sn1 120.1(2) C19 C20 1.354(7) C21 C16 Sn1 122.0(2) C20 C21 1.397(6) C16 C17 C18 120.9(4) C22 C23 1.376 (5) C17 C18 C19 120.6(4) C22 C27 1.387 (5) C18 C19 C20 119.6(4) C22 Sn1 2.121(3) C19 C20 C21 120.5(4) C23 C24 1.387(6) C20 C21 C16 120.3(4) C24 C25 1.361 (8) C23 C22 C27 117. …”

Section: X-ray Analysesmentioning

confidence: 99%

X-Ray and NMR study of tetra- and penta-coordinated stanoxanes derived from trans-cinnamic acid

Ramos-Organillo

Guzmán-Tiburcio

Flores-Bustamante³

et al. 2007

Arkivoc

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We report a new stanoxano polymer structure 1, derived from trans-cinnamic acid and triphenyltin chloride. X-ray structure shows a carboxylated bridge between two tin groups in a linear rearrangement, the pack in the unit cell is conformed by non-classical interactions (D-H···A), because the presence of aromatic rings were observed C-H···π interacting in a supramolecular structure. In solution the compound 1 was compared with tributhyltin-transcinnamete 2, the NMR data shown penta-and tetra-coordinated compounds respectively, both compounds were dissolved in DMSO-d 6 and the tin geometry goes from penta-to hexacoordinated for 1 and from tretracoordinated to pentacoordinated for 2.

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Magnetic double resonance studies of 119Sn chemical shifts in organotin compounds

Cited by 75 publications

References 0 publications

Concerning the 1,5-stereocontrol in tin(iv) chloride promoted reactions of 4- and 5-alkoxyalk-2-enylstannanes: trapping intermediate allyltin trichlorides using phenyllithium

Concerning the 1,5-stereocontrol in tin(iv) chloride promoted reactions of 4- and 5-alkoxyalk-2-enylstannanes: trapping intermediate allyltin trichlorides using phenyllithium

Spectral and Antimicrobial Studies of Organotin(iv) Complexes of Bidentate Schiff Bases Having Nitrogen and Sulphur Donor Systems

X-Ray and NMR study of tetra- and penta-coordinated stanoxanes derived from trans-cinnamic acid

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