Facile Preparation of Hydrazones by the Treatment of Azides with Hydrazines Catalyzed by FeCl<sub>3</sub>·6H<sub>2</sub>O

Barrett, Ian C.; Langille, Jonathan; Kerr, Michael A.

doi:10.1021/jo000708w

Cited by 22 publications

(8 citation statements)

References 5 publications

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“…More recently, iron trichloride has been used in the substitution of azide by dimethyl hydrazine, which allows the formation of hydrazones 159 in very good yields (>81%, eq 45) …”

Section: 2 Nucleophilic Substitutions321 Sn Processesmentioning

confidence: 99%

Iron-Catalyzed Reactions in Organic Synthesis

et al. 2004

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“…More recently, iron trichloride has been used in the substitution of azide by dimethyl hydrazine, which allows the formation of hydrazones 159 in very good yields (>81%, eq 45) …”

Section: 2 Nucleophilic Substitutions321 Sn Processesmentioning

confidence: 99%

Iron-Catalyzed Reactions in Organic Synthesis

et al. 2004

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“…Several relevant hydrazones have recently been prepared in excellent yield by the treatment of azides with hydrazines in the presence of catalytic amounts of FeCl 3 •6H 2 O. 22 By direct amination. 551 By analogy with hydroxylamine-Osulfonic acid, N-methylhydroxylamine-O-sulfonic acid has been applied for preparation of trisubstituted hydrazines.…”

Section: Trisubstituted Hydrazinesmentioning

confidence: 99%

Synthetic methodology for alkyl substituted hydrazines

2001

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“…FTIR/MS analyses were conducted with a Netsch TG209F1 Iris , Bruker Tensor‐27 , Netsch Aeolos QMS 403. The commercially available Ciba® FLAMESTAB® NOR® 116 product was supplied by Ciba Inc. Basel and N‐cyclohexyl sulfamoyl chloride, 3 1, 7 1, 9 12, 10 13, 17 14, 18 15, 19 16, 20 17, and 21 18 were also prepared according to previously described procedures.…”

Section: Experimental Partmentioning

confidence: 99%

Azoalkanes—novel flame retardants and their structure–property relationship

Aubert

Nicolas

Pawelec

et al. 2011

Polymers for Advanced Techs

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A number of symmetrical and unsymmetrical azoalkanes of the general formula R(SN ¼ NSR and related azoxy, hydrazone as well as azine derivatives have been synthesized in order to assess their potential as novel flame retardants for polypropylene alone or in combination with commercially available flame retardants such as alumina trihydrate (ATH), decabromodiphenyl ether (DecaBDE) and tris(3-bromo-2,2-bis(bromomethyl)-propyl)phosphate (TBBPP). The experimental results show that in the series of different sized azocycloalkanes the flame retardant efficacy decreased in the following order: R ¼ cyclohexyl > cyclopentyl > cyclobutyl > cyclooctanyl >> cyclododecanyl. Whereas in the series of aliphatic azoalkanes compounds the efficacy decreased in the following order: R ¼ n-alkyl > tert-butyl > tert-octyl. In addition, also some of the prepared azoxy, azine, and hydrazone derivatives provide flame retardancy to polypropylene films at already very low concentrations (0.25-1 wt%). Noteworthy is that in contrast to other halogen-free radical generators, the azoalkanes are also very effective as flame retardants in polypropylene thick moldings. Interestingly, it was found that 4,4(-bis(cyclohexylazocyclohexyl)-methane) shows a strong synergistic effect with ATH. Thus, in the presence of 0.5 wt% of azoalkane the ATH loading could be reduced from 60 to 25 wt% and still UL94 V-2 rating could be reached. Furthermore, the fire testing data reveal that azoalkanes show a synergistic effect with DecaBDE and when used in conjunction with very low loadings of TBBPP.

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Facile Preparation of Hydrazones by the Treatment of Azides with Hydrazines Catalyzed by FeCl₃·6H₂O

Cited by 22 publications

References 5 publications

Iron-Catalyzed Reactions in Organic Synthesis

Iron-Catalyzed Reactions in Organic Synthesis

Synthetic methodology for alkyl substituted hydrazines

Azoalkanes—novel flame retardants and their structure–property relationship

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Facile Preparation of Hydrazones by the Treatment of Azides with Hydrazines Catalyzed by FeCl3·6H2O

Cited by 22 publications

References 5 publications

Iron-Catalyzed Reactions in Organic Synthesis

Iron-Catalyzed Reactions in Organic Synthesis

Synthetic methodology for alkyl substituted hydrazines

Azoalkanes—novel flame retardants and their structure–property relationship

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Product

Resources

About

Facile Preparation of Hydrazones by the Treatment of Azides with Hydrazines Catalyzed by FeCl₃·6H₂O