<i>p</i>-Toluenesulfonyl Chloride

Whitaker, D. Todd; Whitaker, K. Sinclair; Johnson, Carl R.; Haas, Julia

doi:10.1002/047084289x.rt136.pub2

Cited by 5 publications

(5 citation statements)

References 76 publications

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“…The Apple reaction15 was carried out by using PPh 3 and CBr 4 to replace terminal hydroxyl groups in 7 and 8 by bromo units to produce 9,12‐(BrCH 2 CH 2 CH 2 ) 2 ‐1,2‐ closo ‐C 2 B 10 H 10 ( 11 ) and 8,9,10,12‐(BrCH 2 CH 2 CH 2 ) 4 ‐1,2‐ closo ‐C 2 B 10 H 8 ( 12 ; Schemes and ). Only for 8 was a fourfold tosylation performed with tosyl chloride, NEt 3 as base, and [HNMe 3 ]Cl as catalyst base,16 affording 8,9,10,12‐(TsOCH 2 CH 2 CH 2 ) 4 ‐1,2‐ closo ‐C 2 B 10 H 8 ( 13 ) in good yield (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Globular Precursors

Teixidor

Sillanpää

Pepiol

et al. 2015

Chemistry A European J

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o-Carborane (C2 B10 H12 ) was adapted to perform as the core of globular macromolecules, dendrons or dendrimers. To meet this objective, precisely defined substitution patterns of terminal olefin groups on the carborane framework were subjected to Heck cross-coupling reactions or hydroboration leading to hydroxyl terminated arms. These led to new terminal groups (chloro, bromo, and tosyl leaving groups, organic acid, and azide) that permitted ester production, click chemistry, and oxonium ring opening to be performed as examples of reactions that demonstrate the wide possibilities of the globular icosahedral carboranes to produce new dendritic or dendrimer-like structures. Polyanionic species were obtained in high yield through the ring-opening reaction of cyclic oxonium compound [3,3'-Co(8-C4 H8 O2 -1,2-C2 B9 H10 )(1',2'-C2 B9 H11 )] by using terminal hydroxyl groups as nucleophiles. These new polyanionic compounds that contain multiple metallacarborane clusters at their periphery may prove useful as new classes of compounds for boron neutron capture therapy with enhanced water solubility and as cores to make a new class of high-boron globular macromolecules.

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Section: Resultsmentioning

confidence: 99%

Synthesis of Globular Precursors

Teixidor

Sillanpää

Pepiol

et al. 2015

Chemistry A European J

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“…Furthermore, alcohol groups were converted to tosylate groups by performing the reaction of 3 with tosyl chloride, Net 3 as a base, and [HNMe 3 ]Cl as a catalyst [ 43 ], obtaining 9,10-(TsOCH 2 CH 2 CH 2 ) 2 -1,7- closo -C 2 B 10 H 10 , 7 , in 85% yield.…”

Section: Resultsmentioning

confidence: 99%

“…The electrophilic substitution of the o -carborane led to the formation of the tetrasubstituted 8,9,10,12-I 4 -1,2- closo -C 2 B 10 H 8 compound [ 5 , 42 , 43 ] in which the B-I vertexes reside at the compacted adjacent positions antipodal to the two cluster carbon C c atoms. Conversely, the iodination electrophilic substitution takes place only at the B(9) and B(10) vertexes of the m -isomer.…”

Section: Resultsmentioning

confidence: 99%

m-Carborane as a Novel Core for Periphery-Decorated Macromolecules

et al. 2020

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Closo m-C2B10H12 can perform as a novel core of globular periphery-decorated macromolecules. To do this, a new class of di and tetrabranched m-carborane derivatives has been synthesized by a judicious choice of the synthetic procedure, starting with 9,10-I2-1,7-closo-C2B10H10. The 2a-NPA (sum of the natural charges of the two bonded atoms) value for a bond, which is defined as the sum of the NPA charges of the two bonded atoms, matches the order of electrophilic reaction at the different cluster bonds of the icosahedral o-and m- carboranes that lead to the formation of B-I bonds. As for m-carborane, most of the 2a-NPA values of B-H vertexes are positive, and their functionalization is more challenging. The synthesis and full characterization of dibranched 9,10-R2-1,7-closo-carborane (R = CH2CHCH2, HO(CH2)3, Cl(CH2)3, TsO(CH2)3, C6H5COO(CH2)3, C6H5COO(CH2)3, N3(CH2)3, CH3CHCH, and C6H5C2N3(CH2)3) compounds as well as the tetrabranched 9,10-R2-1,7-R2-closo-C2B10H8 (R = CH2CHCH2, HO(CH2)3) are presented. The X-ray diffraction of 9,10-(HO(CH2)3)2-1,7-closo-C2B10H10 and 9,10-(CH3CHCH)2-1,7-closo-C2B10H10, as well as their Hirshfeld surface analysis and decomposed fingerprint plots, are described. These new reported tetrabranched m-carborane derivatives provide a sort of novel core for the synthesis of 3D radially grown periphery-decorated macromolecules that are different to the 2D radially grown core of the tetrabranched o-carborane framework.

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“…sulfonylation of primary or secondary amine in presence of base resulting in nucleophilic attack by amine. For sulfonylationtosyl chlorides were used [13] and base were used for neutralization of generated HCl, i.e. pyridine in synthesis of sulfonylmethylamide [14].…”

Section: General Proceduresmentioning

confidence: 99%

Synthesis and characterization of novel sulfonamides derivatives and their antimicrobial, antioxidant and cytotoxicity evaluation

Rehman¹,

Qadir²,

Ali³

et al. 2018

Bull. Chem. Soc. Eth.

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ABSTRACT. Five novel sulfonamides derivatives HR5-HR8 and HR14 were synthesized by sulfonylation of primary or secondary amine in the presence of base through nucleophilic substitution reaction. Structural elucidation was carried out through FT-IR, UV, 1 H NMR, MS and elemental analysis. Prepared compounds were evaluated against pathogenic strains of bacteria (S. aureus and E. coli) and fungi (A. flavous and A. nyger). Results were compared against standard antifungal and bacterial drug already available in market (isoconazole and sulfmethoxazole). It was found that compound HR14 showed good activity with MIC 1.5 µg/mL and 2.0 µg/mL for S. aurues and E. coli, respectively. While HR5 showed best antifungal activity with zone of inhibition 27.2+0.12 mm (MIC: 5.25 µg/mL) and 18.1+0.12 mm (MIC: 12.5 µg/mL) against A. flavous and A. nyger, respectively. Synthesized compounds were also tested for their in vitro antioxidant activity by using DDPH. Amongst all compounds HR5 was found to have potential activity with 15.60% antioxidant activity at 6 mM concentration.

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p-Toluenesulfonyl Chloride

Cited by 5 publications

References 76 publications

Synthesis of Globular Precursors

Synthesis of Globular Precursors

m-Carborane as a Novel Core for Periphery-Decorated Macromolecules

Synthesis and characterization of novel sulfonamides derivatives and their antimicrobial, antioxidant and cytotoxicity evaluation

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