A STANDARDIZATION OF THE SANDMEYER REACTION, WITH SPECIAL APPLICATIONS<sup>1</sup>

Fry, H. Shipley; Grote, I.W.

doi:10.1021/ja01414a025

Cited by 12 publications

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“…Polar protic and aprotic solvents are most often employed for transformations involving diazonium salts including water, CH 3 CN, and DMF . Sandmeyer reactions are traditionally conducted in their respective aqueous halide acid solutions as per the 1926 preparation described by Fry and Grote . Aqueous halide acids are still technically halogenated solvents and suffer from the same issues regarding waste disposal and incineration (see section ).…”

Section: Viable Alternatives To Chlorinated Solvents For Different Si...mentioning

confidence: 99%

“…253 Sandmeyer reactions are traditionally conducted in their respective aqueous halide acid solutions as per the 1926 preparation described by Fry and Grote. 254 Aqueous halide acids are still technically halogenated solvents and suffer from the same issues regarding waste disposal and incineration (see section 3.1). Filimonov et al have shown that it is possible to react diazonium tosylate salts with either KI, KBr, or NaNO 2 in water or MeOH (for NaNO 2 reaction) at room temperature to give the respective aryl halide or nitro compound.…”

Section: Commonly Employed Transformations In Medicinal Chemistrymentioning

confidence: 99%

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Chlorinated Solvents: Their Advantages, Disadvantages, and Alternatives in Organic and Medicinal Chemistry

Jordan

Stoy

Sneddon³

2020

Chem. Rev.

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Chlorinated solvents were once, and in many places are still, ubiquitous in chemistry laboratories. This review explores the properties that led to such widespread use, why there is now an increasing drive to minimize usage, and what alternatives are currently available. CONTENTS 1.0. Introduction 1583 2.0. Advantages of Chlorinated Solvents 1586 2.1. Physico-Chemical Properties and Relevant Applications 1586 2.1.1.

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Section: Viable Alternatives To Chlorinated Solvents For Different Si...mentioning

confidence: 99%

Section: Commonly Employed Transformations In Medicinal Chemistrymentioning

confidence: 99%

Chlorinated Solvents: Their Advantages, Disadvantages, and Alternatives in Organic and Medicinal Chemistry

Jordan

Stoy

Sneddon³

2020

Chem. Rev.

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“…9,9-Dimethyl-9-silafluorene. The needed 2,2'-dibromobiphenyl was prepa red by the.following procedure: o-nitroaniline (140 g, 1 mol) was co nverted by the Sandmeyer reaction 15 into o-chloronitrobenzene (123 g, 0'78 mol), m.p. 32°e.…”

Section: Experimental Chemicalsmentioning

confidence: 99%

Organosilicon compounds. L. Pyrolysis of phenyldimethylsilane

Mareš¹,

Chvalovský²

1967

Collect. Czech. Chem. Commun.

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The predominant products of pyrolysis of phenyldimethylsilane, studied in a through-Aow reactor, have proved to be diphenyldimethylsilane, 9,9-dimethyl-9-silafluorene, and polymers: benzene and toluene are formed to a small extent. For comparison we have studied the kinetics of pyrolysis of p-tolyldimethylsilane, giving rise to the analogous p-methylsubstituted products, and of diphenyldimethylsilane, which produces benzene , toluene, phenyldimethylsilane and polymers. On the basis of the results obtained a chain radical mechanism of pyrolysis of phenyldimethylsilane is proposed and discussed.The thermal stability of silicon hydrides has thus far been paid little attention. The literature l describes the pyrolyses of silane, disilane, higher silanes and ethylsilanes (CzHs)n SiH 3 -n , but not of siJanes with Si-aryl bonds. Theoretically the stability of silanes should be in a direct relation to the dissociation energies of the bonds present in the molecule of the compound considered. Unfortunately, the dissociation energies of the bonds Si-R where R = CH 3 , C6HS and H have not been safely determined or measured at all. Measured values of the dissociation energies of the bonds present in the molecules of phenyldimethylsilane and tolyldimethylsilane are listed in Table]. They suggest that in the initiation stage of pyrolysis of these compounds there will probably occur cleavage of the bonds between silicon and phenyl, hydrogen or methyl, the bond Si-C6Hs being probably the first to split. As the dissociation energy of the bond Si-C6Hs has been calculated from the combustion heat of tetraphenylsilane, the value obtained (51'3 kcal/mol) is most probably distorted by the possible mesomeric shifts, whose effect in phenyldimethylsilane is probably weaker than in tetraphenylsilane. Thus it is difficult to predict which of the silicon bonds considered will prove the most labile.

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“…Soc,, 79, 1458 (1957). (10) Boiling points are uncorrected. Infrared spectra were obtained using a Beckman IR-4 spectrophotometer.…”

Section: ---^(mentioning

confidence: 99%

Amines Derived from Dihalopropenes. III.^1a Dehydrobromination of cis- and trans-N-(3-Bromoallyl)-n-butylamine^1b,c

Bottini¹,

King²,

Lucas³

1962

J. Org. Chem.

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The reactions of cis-and ¿rans--(3-bromaiiyI)n-butylamine (cis-and ¿rans-) with sodium amide in liquid ammonia were investigated because it appeared that these reactions could proceed by one or more of at least three routes. These routes included ^-elimination (1), which would yield Nn-butyipropargylamine (II), ^-fragmentation (2), which would yield acetylene, formaldehyde, and nbutylamine (III), and cyclization (3), which would yield N-n-butylazetine (IV).imines are now known to be formed via an elimina-

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A STANDARDIZATION OF THE SANDMEYER REACTION, WITH SPECIAL APPLICATIONS¹

Cited by 12 publications

References 0 publications

Chlorinated Solvents: Their Advantages, Disadvantages, and Alternatives in Organic and Medicinal Chemistry

Chlorinated Solvents: Their Advantages, Disadvantages, and Alternatives in Organic and Medicinal Chemistry

Organosilicon compounds. L. Pyrolysis of phenyldimethylsilane

Amines Derived from Dihalopropenes. III.^1a Dehydrobromination of cis- and trans-N-(3-Bromoallyl)-n-butylamine^1b,c

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A STANDARDIZATION OF THE SANDMEYER REACTION, WITH SPECIAL APPLICATIONS1

Cited by 12 publications

References 0 publications

Chlorinated Solvents: Their Advantages, Disadvantages, and Alternatives in Organic and Medicinal Chemistry

Chlorinated Solvents: Their Advantages, Disadvantages, and Alternatives in Organic and Medicinal Chemistry

Organosilicon compounds. L. Pyrolysis of phenyldimethylsilane

Amines Derived from Dihalopropenes. III.1a Dehydrobromination of cis- and trans-N-(3-Bromoallyl)-n-butylamine1b,c

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A STANDARDIZATION OF THE SANDMEYER REACTION, WITH SPECIAL APPLICATIONS¹

Amines Derived from Dihalopropenes. III.^1a Dehydrobromination of cis- and trans-N-(3-Bromoallyl)-n-butylamine^1b,c