A Simple Method for the Direct Oxidation of Aromatic Amines to Nitroso Compounds<sup>1</sup>

Holmes, Richard R.; Bayer, Raymond P.

doi:10.1021/ja01498a054

Cited by 97 publications

(25 citation statements)

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“…2,6-Dichloro-nitrosobenzene (DCNB) was synthesized by oxidation of 2,6-dichloroaniline (Nacalai Tesque Co., Ltd.). 9 Cis 1,4-polybutadiene was purchased from 1 To whom correspondence should be addressed.…”

Section: Methodsmentioning

confidence: 99%

Characterization of Grafted Polybutadiene on a Poly(tetrafluoroethylene) Surface of Extremely Low Grafting Ratio

Yamamoto

Shimada

Sakaguchi³

et al. 1997

Polym J

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ABSTRACT:Butadiene monomer (BD) was block copolymerized by the tmtlatwn of mechanoradicals formed by mechanical fracture of poly(tetrafluoroethylene) (PTFE) powder. Polybutadiene (PBD) propagating radicals are much more stable and much mobile above melting temperature of butadiene monomer. In order to determine extremely low grafting ratio, nitroxide free radicals produced by reactions of 2,6-dichloronitrosobenzene with double bonds in PBD on PTFE are quantitatively detected. The determination of 10-3 -10-1 (%)of grafting ratio was possible by the spin labeling method and the grafted chains were regarded as isolated chains. The extremely low grafting ratio could not be detected by other methods. The estimated number average molecular weight ofthe grafted chain was strongly dependent on the pressure ofBD monomer.

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Section: Methodsmentioning

confidence: 99%

Characterization of Grafted Polybutadiene on a Poly(tetrafluoroethylene) Surface of Extremely Low Grafting Ratio

Yamamoto

Shimada

Sakaguchi³

et al. 1997

Polym J

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“…In an adaptation of an earlier procedure, 35 2,6-dichloroaniline was oxidized to 2,6-dichloronitrobenzene (18) with peroxyacetic acid according to a general method. 36 Subsequent reaction of 18 with an ethanolic solution of 1-propanethiolate resulted in a double substitution to yield 2,6-bispropylthionitrobenzene (19) in analogy to a similar literature procedure. 37 The combined yield for 19 was 28% based on the starting amine.…”

Section: Synthesis Of 2-bromo-3-propylthiobenzaldehyde 4bmentioning

confidence: 99%

Preparation and NMR Analysis of 2,6-Heterodifunctional Halobenzenes as Precursors for Substituted Biphenyls

2000

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Abstract-Preparation and complete characterization of 16 2,6-disubstituted halobenzenes, including nine new compounds, from two common starting materials is described. Seven of the new compounds contain one or two propylthio groups, which have been introduced in two ways. Direct reaction of arenediazonium salts with 1-propanethiolate gives yields comparable to those obtained in a three-step method through sulfonyl chlorides. The 1 H-and 13 C NMR chemical shifts of 17 1,2,3-trisubstituted benzenes have been correlated with the predicted values and the observed trends explained using commonly available modeling packages. ᭧

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“…NMR spectra were recorded on a Bruker DRX instru ment (500 MHz) in DMSO d6 with Me 4 Si as the internal stan dard. The course of the reactions was monitored, and the purity of the compounds obtained was checked, by TLC on Silufol UV 254 plates.…”

mentioning

confidence: 99%

Reactions of polyhalonitrosoarenes with phenylacetylene

et al. 2010

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A Simple Method for the Direct Oxidation of Aromatic Amines to Nitroso Compounds¹

Cited by 97 publications

References 1 publication

Characterization of Grafted Polybutadiene on a Poly(tetrafluoroethylene) Surface of Extremely Low Grafting Ratio

Characterization of Grafted Polybutadiene on a Poly(tetrafluoroethylene) Surface of Extremely Low Grafting Ratio

Preparation and NMR Analysis of 2,6-Heterodifunctional Halobenzenes as Precursors for Substituted Biphenyls

Reactions of polyhalonitrosoarenes with phenylacetylene

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A Simple Method for the Direct Oxidation of Aromatic Amines to Nitroso Compounds1

Cited by 97 publications

References 1 publication

Characterization of Grafted Polybutadiene on a Poly(tetrafluoroethylene) Surface of Extremely Low Grafting Ratio

Characterization of Grafted Polybutadiene on a Poly(tetrafluoroethylene) Surface of Extremely Low Grafting Ratio

Preparation and NMR Analysis of 2,6-Heterodifunctional Halobenzenes as Precursors for Substituted Biphenyls

Reactions of polyhalonitrosoarenes with phenylacetylene

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A Simple Method for the Direct Oxidation of Aromatic Amines to Nitroso Compounds¹