Catalysis of the Diels-Alder Reaction by Organotin Halides

Gabriele, Martin; Kuivila, Henry G.; Cochran, John C.

doi:10.1515/mgmc.1998.21.4.207

Cited by 3 publications

(2 citation statements)

References 7 publications

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“…This holds especially for the o -phenylene-bridged dimercury 12 and disilicon species of type A . The power of 1,8-bis(alkylstannyl)naphthalene in alkylation reactions has been demonstrated recently 14a14b…”

Section: Introductionmentioning

confidence: 99%

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o-Bis(haloorganostannyl)benzenes As Powerful Bidentate Lewis Acids toward Halide Ions

Altmann¹,

Jurkschat²,

Schürmann³

et al. 1998

Organometallics

102

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The synthesis of the o-phenylene-bridged ditin species o-C 6 H 4 (SnXMe 2 ) 2 (2, X ) Cl; 4, X ) F) and o-C 6 H 4 (SnCl 2 Me) 2 (3) is reported and the crystal structures of [o-C 6 H 4 (SnClMe 2 ) 2 ‚ Cl] -[(Ph 3 N) 2 P] + (5) and [o-C 6 H 4 (SnClMe 2 ) 2 ‚F] -[K‚C 20 H 24 O 6 ] + (7) are described. Variabletemperature 119 Sn and 19 F NMR studies indicate that 2 and 4 act as bidentate Lewis acids toward chloride and fluoride ions exclusively forming the stable anionic 1:1 complexes 5, 7, and [o-C 6 H 4 (SnFMe 2 ) 2 ‚F] -[Et 4 N] + ( 8). No formation of dianionic 1:2 adducts was observed even with excess of halide ions. The affinity of 2 toward fluoride is greater than toward chloride. Reaction of 2 with HMPA gives the neutral complex o-C 6 H 4 (SnClMe 2 ) 2 ‚(Me 2 N) 3 PO (10), the crystal structure of which is also described.

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Section: Introductionmentioning

confidence: 99%

“…The power of 1,8-bis(alkylstannyl)naphthalene in alkylation reactions has been demonstrated recently 14a14b …”

Section: Introductionmentioning

confidence: 99%

o-Bis(haloorganostannyl)benzenes As Powerful Bidentate Lewis Acids toward Halide Ions

Altmann¹,

Jurkschat²,

Schürmann³

et al. 1998

Organometallics

102

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Cyclic Dinuclear Organotin Cations Stabilized by Bulky Substituents

et al. 2015

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The syntheses of sterically congested 2,2-bis-(diorganochloridostannyl)propane, Me 2 C(SnClR 2 ) 2 (1; R = CH-(SiMe 3 ) 2 ), the related salts [cyclo-{Me 2 C(SnR 2 ) 2 X}B(Ar F ) 4 ] (2, X = Cl; 3, X = OAc; 4, X = OH; Ar F = 3,5-(CF 3 ) 2 C 6 H 3 ), and the fourmembered-ring cyclo-{Me 2 C(SnR 2 ) 2 O} (5) are reported. The compounds have been characterized by elemental and EDX analyses, 1 H, 11 B, 13 C, 19 F, 29 Si, and 119 Sn NMR and IR spectroscopy, electrospray ionization mass spectrometry, and single-crystal X-ray diffraction analysis.

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Synthesis, Characterization and Antifungal Assessment of Optically Active Bis-organotin Compounds Derived from (S)-BINOL Diesters

Costantino¹,

Neudörfl²,

Ocampo³

et al. 2019

CHEM

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Background: Organotin(IV) derivatives have appeared recently as potential biologically active metallopharmaceuticals exhibiting a variety of therapeutic activities. Hence, it is important to study the synthesis of new organotin compounds with low toxicity that may be of pharmacological interest. Objectives: This study focuses on the synthesis of new bis-stannylated derivatives with C2 symmetry that could be tested as antifungal agents against two clinical important fungal species, Cryptococcus neoformans and Candida albicans. Methods: The radical addition of triorganotin hydrides (R3SnH) and diorganotin chlorohydrides (R2ClSnH) to bis-α,β-unsaturated diesters derived from (S)-BINOL led to the corresponding new bis-stannylated derivatives with C2 symmetry. Nine pure organotin compounds were synthesized with defined stereochemistry. Four of them were enantiomerically pure and four were diastereoisomeric mixtures. Results: All new organotin compounds were fully characterized, those with phenyl ligands bonded to tin were the most active compounds against both the strains (Cryptococcus neoformans and Candida albicans), with activity parameters of IC50 close to those of the reference drug (amphotericin B). Conclusion: Nine pure organotin compounds with C2 symmetry were synthesized with defined stereochemistry and their antifungal properties were tested against two clinical important fungi with IC values close to those of the reference drug. The structure-containing preferably two or three phenyl groups joined to the tin atom were highly active against both the strains compared with those possessing tri-n-butyl groups.

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Catalysis of the Diels-Alder Reaction by Organotin Halides

Abstract: Organotin halides catalyze the Diels-Alder reaction between isoprene and methyl vinyl ketone. The catalytic activity is a function of the number of proximate tin atoms in the molecule and the extent of halogen substitution on tin.

Cited by 3 publications

References 7 publications

o-Bis(haloorganostannyl)benzenes As Powerful Bidentate Lewis Acids toward Halide Ions

o-Bis(haloorganostannyl)benzenes As Powerful Bidentate Lewis Acids toward Halide Ions

Cyclic Dinuclear Organotin Cations Stabilized by Bulky Substituents

Synthesis, Characterization and Antifungal Assessment of Optically Active Bis-organotin Compounds Derived from (S)-BINOL Diesters

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