Solid-state organic reactions proceeding by pulverization: Oxidation and halogenation with iodosobenzene and inorganic solid-supports

Sohmiya, Hajime; Kimura, Takeshi; Fujita, Mitsue; Ando, Takashi

doi:10.1016/s0040-4020(98)00844-8

Cited by 28 publications

(24 citation statements)

References 53 publications

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“…was used in transformations of olefins (B104, Scheme B25). 1,1-Diphenylethene was hydrobrominated (B105a) in 27% yield, bromine addition to trans-stilbene B104b was observed in 39% yield, while oxidation, resulting in the formation of 47% of B105C was reported in the case of 1,1,2-triphenylethene B104c [69]. Bromination of 1,2-diphenylethyne resulted in the formation of the 1,2-dibromoethene derivative in 51% yield [69].…”

Section: Transformation With the Bromide/oxidant Systemmentioning

confidence: 99%

“…Trans-stilbene (C45a) gave vicinal dichloride (C46a), while hydroxychlorination took place in the case of 1,1-diphenyl (C45b) and 1,1,2-triphenyl ethene (C45c, Scheme C11). Chlorination also took place when treating 1,2-diphenylacetilene and anthracene with this reagent and 1,2-diphenyl-1,2-dichloroethene (C48) or 9,10-dichloro anthracene (C50) were isolated, respectively [69].…”

Section: Transformations With the Chloride/oxidizer Systemmentioning

confidence: 99%

“…The oxidation chlorination approach under SFRC using the HCl-SiO 2 /PhIO reaction system [69] was aplied for the chlorination of tetraphenyl ethene (C52) and the corresponding epoxide C55 was isolated in high yield (Scheme C12). Oxidative demethylation was observed in the case of 9,10-dimethoxy anthracene (C51), while the type of functionalisations of sulfides and disulfides depended on structure of the substrate.…”

Section: Transformations With the Chloride/oxidizer Systemmentioning

confidence: 99%

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Introduction of Halogen Atoms into Organic Compounds Under Solvent- Free Reaction Conditions

Pravst¹,

Zupan²,

Stavber

2009

COC

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Avoiding volatile and toxic organic solvents during each particular phase of synthetic protocols should become important goal of chemical synthesis designers in academia and particularly in the industrial research community. Solvent-free reaction conditions (SFRC) are becoming a widely used experimental technique for the selective and efficient introduction of halogen atoms into organic compounds. The different approaches to the preparation of halosubstituted organic molecules using equimolar amount of the substrate and reagent under SFRC are reviewed and evaluated. Fluorination of various types of organic compounds under SFRC using fluorine gas, N-F reagents, and hydrogen or metal fluorides is compiled. Chloro-, bromo-or iodofunctionalisation under SFRC using molecular halogens, N-halosuccinimides, hydrogen or others halides is reviewed. Oxidative halogenations of comprehensive types of organic compounds under SFRC are evaluated.

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Section: Transformation With the Bromide/oxidant Systemmentioning

confidence: 99%

Section: Transformations With the Chloride/oxidizer Systemmentioning

confidence: 99%

Section: Transformations With the Chloride/oxidizer Systemmentioning

confidence: 99%

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Introduction of Halogen Atoms into Organic Compounds Under Solvent- Free Reaction Conditions

Pravst¹,

Zupan²,

Stavber

2009

COC

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“…The excess of SO 2 Cl 2 was hydrolyzed by the addition of water (10 mL). The crude product was extracted with 3 × 5 mL of EtOAc, and 2.64 g of 2b [16] …”

Section: Synthesis Of Butanesulfonyl Chloride (2b)mentioning

confidence: 99%

“…The excess of SO 2 Cl 2 was hydrolyzed by the addition of water (10 mL). The crude product was extracted with 3 × 5 mL of EtOAc and 2.15 g of 2f [16] Synthesis of 3,3,4,4,5,5,6,6,6-nonafluorohexanesulfonyl Chloride (2h). Twenty-nine grams (95 mmol) of 1h dissolved in a mixture of 27 mL (475 mmol) of acetic acid and 2.6 mL (142.5 mmol) of water was stirred 1.5 h at 50…”

Section: Synthesis Of Octanesulfonyl Chloride (2f)mentioning

confidence: 99%