Unsaturated Sulfonic Acids. V.<sup>1</sup> Addition of Diazomethane and Phenyl Azide to Derivatives of Ethylenesulfonic Acid and its Homologs<sup>2</sup>

Rondestvedt, Christian S.; Chang, Pauline K.

doi:10.1021/ja01629a036

Cited by 64 publications

(23 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Vinyl polymerization : Though it is not possible t o decide which of the two hydrogen transfer processes, (3) or (4) may obtain, distinction of (2) from (3) or (4) could be made b y infrared spectroscopy. Intensity of absorption characteristic of N-H bond should be smaller for polymer obtained b y (3) or (4) than for polymer obtained by (2). As shown in Fig.…”

Section: Ionic Polymerizationmentioning

confidence: 82%

Polymerization of N‐acryloylbenzhydrazide and selective cation scavenging by the polymer

Tazuke

Nakamura

1966

Makromol. Chem.

View full text Add to dashboard Cite

A new monomer, N-acryloylbenzhydrazide was synthesized and its polymerizability was investigated. Fhe monomer is easily polymerized by radical as well as by anionic initiators, but not by cationic ones. A possibility of hydrogen transfer polymerization by an anionic mechanism is suggested. y-Ray irradiation is also an effective way to polymerize the monomer in the solid state. Monomer reactivity ratios for radical copolymerization of the monomer with styrene and acrylonitrile,are rl = 1.40 i 0.05, r 2 4 5 f 0.05 and rl = 0.33 & 0.08,The polymer forms stable chelates with transition metal ions, in particular with cupric ion, when the polymer is suspended in methanol containing metal salts, indicating a possibility of application as a selective cation scavenging resin. 0.08, respectively, where M, is styrene or acrylonitrile. ZUSAMMENFASSUNG:Ein neues Monomeres, N-Acryloylbenzhydrazid (ABH) wurde hergestellt und auf seine Polymerisierbarkeit untersucht. Das Monomere kann leicht radikalisch und anionisch, jedoch nicht kationisch polymerisiert werden. Durch y-Strahlen kann die Polymerisation in Substanz (fest) erfolgen.Bei der anionischen Polymerisation wird die Moglithkeit einer Wasserstoffiibertragung in Betracht gezogen. Die ReaktivitHtsverhaltnisse fiir die radikalische Copolymerisation von ABH mit Styrol und Acrylnitril sind r, = 1,40 f 0,05 und r2 = 0,65 0,05 bzw. r, = 0,33 f 0,08 und r2 = 0,23 f 0,08.Poly-ABH bildet in methanolischer Suspension mit Ubergangsmetallionen, besonders mit Cuz+-Ionen, stabile Chelate. Hierin liegt eine Moglichkeit fiir eine selektive Kationenabsorption.

show abstract

Section: Ionic Polymerizationmentioning

confidence: 82%

Polymerization of N‐acryloylbenzhydrazide and selective cation scavenging by the polymer

Tazuke

Nakamura

1966

Makromol. Chem.

View full text Add to dashboard Cite

show abstract

“…Rondestvedt and Chang demonstrated that 11 undergoes direct Michael addition to ESCl (reflux in benzene,6h) to give the sulfonate adduct 10 in 99 %yield [presumed to arise through hydrolysis of the unstable sulfonyl chloride (9)]. [20,36] Under equivalent reaction conditions with ESF,w eo bserve no such reaction. However,upon heating at 100 8 8CinEtOAc with 3.00 equivalents of HCl for 4hours,the triazole addition products (14 a-e)c ould indeed be obtained in good yield (Scheme 3).…”

Section: Angewandte Chemiementioning

confidence: 99%

“…[24,25] ESF offers many other advantages over ESCl in terms of stability and properties ( Figure 1C), [26] and has been described as "the most perfect Michael acceptor ever found". [24,27] Studies commenced by performing ar eaction between ESF and 6 following the method of Rondestvedt and Chang (cf.ESCl): [20] stirring in benzene at ambient temperature for 5 hours in as ealed tube.U nder these reaction conditions,n o products were observed and starting materials fully recovered. However,raising the reaction temperature to 100 8 8Cand stirring for af urther 5hours, 11 was isolated in 47 %y ield along with unreacted starting materials (see the Supporting Information).…”

mentioning

confidence: 99%

Metal‐Free Synthesis of Functional 1‐Substituted‐1,2,3‐Triazoles from Ethenesulfonyl Fluoride and Organic Azides

et al. 2019

View full text Add to dashboard Cite

The boom in growth of 1,4‐disubstituted triazole products, in particular, since the early 2000’s, can be largely attributed to the birth of click chemistry and the discovery of the CuI‐catalyzed azide–alkyne cycloaddition (CuAAC). Yet the synthesis of relatively simple, albeit important, 1‐substituted‐1,2,3‐triazoles has been surprisingly more challenging. Reported here is a straightforward and scalable click‐inspired protocol for the synthesis of 1‐substituted‐1,2,3‐triazoles from organic azides and the bench stable acetylene surrogate ethenesulfonyl fluoride (ESF). The new transformation tolerates a wide selection of substrates and proceeds smoothly under metal‐free conditions to give the products in excellent yield. Under controlled acidic conditions, the 1‐substituted‐1,2,3‐triazole products undergo a Michael addition reaction with a second equivalent of ESF to give the unprecedented 1‐substituted triazolium sulfonyl fluoride salts.

show abstract

“…The nitrous acid formed in situ can diazotize as well as oxidize the amine hydrochloride to rub-azoic acid [5,18]. Both of the reactions proceeded competitively.…”

Section: Synthesis:-mentioning

confidence: 99%

A Kinetic Study of Rubazoic Acid Formation Derived From 4-Amino-1(4-Sulphophenyl) 3-Methyl-2-Pyrazolin-5-One.

Hussain¹,

Khan²,

Ahmad³

et al. 2017

IJAR

View full text Add to dashboard Cite

Unsaturated Sulfonic Acids. V.¹ Addition of Diazomethane and Phenyl Azide to Derivatives of Ethylenesulfonic Acid and its Homologs²

Cited by 64 publications

References 0 publications

Polymerization of N‐acryloylbenzhydrazide and selective cation scavenging by the polymer

Polymerization of N‐acryloylbenzhydrazide and selective cation scavenging by the polymer

Metal‐Free Synthesis of Functional 1‐Substituted‐1,2,3‐Triazoles from Ethenesulfonyl Fluoride and Organic Azides

A Kinetic Study of Rubazoic Acid Formation Derived From 4-Amino-1(4-Sulphophenyl) 3-Methyl-2-Pyrazolin-5-One.

Contact Info

Product

Resources

About

Unsaturated Sulfonic Acids. V.1 Addition of Diazomethane and Phenyl Azide to Derivatives of Ethylenesulfonic Acid and its Homologs2

Cited by 64 publications

References 0 publications

Polymerization of N‐acryloylbenzhydrazide and selective cation scavenging by the polymer

Polymerization of N‐acryloylbenzhydrazide and selective cation scavenging by the polymer

Metal‐Free Synthesis of Functional 1‐Substituted‐1,2,3‐Triazoles from Ethenesulfonyl Fluoride and Organic Azides

A Kinetic Study of Rubazoic Acid Formation Derived From 4-Amino-1(4-Sulphophenyl) 3-Methyl-2-Pyrazolin-5-One.

Contact Info

Product

Resources

About

Unsaturated Sulfonic Acids. V.¹ Addition of Diazomethane and Phenyl Azide to Derivatives of Ethylenesulfonic Acid and its Homologs²