Reactivities of amino and aminium radicals: oxidative photoaddition of tetramethyl-2-tetrazene to olefins

Magdzinski, Leon J.; Chow, Yuan L.

doi:10.1021/ja00476a030

Cited by 10 publications

(9 citation statements)

References 5 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The mechanisms of these several reactions and the reasons for their differences are being sought. 2>S+-+ CH3COCH3 ->S+CH2COCH3 + >S + H+ (10) >S+. + CH2=C(OH)CH3 >S+CH2C(OH)CH3 (11) 13 Experimental Section…”

Section: Resultsmentioning

confidence: 96%

Ion radicals. 43. Addition of thianthrene and phenoxathiin cation radicals to alkenes and alkynes

Shine¹,

Bandlish²,

Mani³

et al. 1979

J. Org. Chem.

View full text Add to dashboard Cite

Section: Resultsmentioning

confidence: 96%

Ion radicals. 43. Addition of thianthrene and phenoxathiin cation radicals to alkenes and alkynes

Shine¹,

Bandlish²,

Mani³

et al. 1979

J. Org. Chem.

View full text Add to dashboard Cite

“…Besides, thianthrene cation radical is a highly reactive species and can react in a number of ways. [1] Generally, it will react with a nucleophilic species (ZH) with hydrogen to generate a Bronsted acid, HX, which can initiate the polymerization reactions.…”

Section: Resultsmentioning

confidence: 99%

“…[2] However, polymerization of alkenes promoted by addition of a cation radical is not a common reaction. [1] The cationic polymerization of vinyl and heterocyclic derivatives, which usually proceeds via cationic chain carriers, can be initiated using various agents including Lewis and Bronsted acids, oxonium salts and using ionizing radiation. [3] The persistent carbocation radical-initiated polymerization was first reported.…”

Section: Introductionmentioning

confidence: 99%

Polymerization of Vinyl Monomers Initiated by Thianthrene Cation Radical with Potential Biological Activity

Lee¹,

Kim²,

Park³

et al. 2012

Journal of the Chosun Natural Science

View full text Add to dashboard Cite

Polymerization of vinyl monomers is promoted by thianthrene cation radical as a part of our research concerning the reactions of various agents with readily isolable, yet highly reactive species and elucidate the biological activity. Thianthrene cation radical initiated the homopolymerization and copolymerization of styrene and ethyl vinyl ether. The polymerization yields decreased as the concentration of phenylacetylene or diphenylethylene increased. Such polymereization by cationic thianthrene radical could provide some clues for the reaction in living animals. Comments on possible polymerization mechanisms were suggested.

show abstract

“…With a NÀ N=NÀ N topology, 2-Tetrazenes form a class of 4 N polynitrogen compounds with important properties. They can be used as reagents for amino-hydroxylations of olefins, [1] initiators for radical polymerization, [2][3][4][5][6] or ligands for transition metals. [7][8][9][10] When the molecules are stripped from most substituents, tetrazenes become energetic and could be used for propulsion [11,12] or pyrotechnic [13][14][15][16] purposes.…”

Section: Introductionmentioning

confidence: 99%

Catalytic Aerobic Oxidation of Hydrazines into 2‐Tetrazenes

2022

View full text Add to dashboard Cite

Dedicated to Holger Braunschweig on his 60th birthday, for his continued support and inspiration.We report a catalytic formation of 2-tetrazenes by copper (ii) promoted oxidation of hydrazines in the presence of bipyridine ligands, that uses air or dioxygen as terminal oxidant. The method was applied to a series of hydrazines, delivering symmetrical tetrazenes, which were previously prepared using toxic or stoichiometric oxidants. The catalytic reaction could be used for the formation of a cyclic tetrazene from a bishydrazine, presumably with the help of a chelation of the substrate to the catalytic metal, which favored cyclization over oligomerization. Finally, the method could be used to prepare dissymmetric structures, albeit in the presence of an excess of one of the hydrazines.

show abstract

Reactivities of amino and aminium radicals: oxidative photoaddition of tetramethyl-2-tetrazene to olefins

Cited by 10 publications

References 5 publications

Ion radicals. 43. Addition of thianthrene and phenoxathiin cation radicals to alkenes and alkynes

Ion radicals. 43. Addition of thianthrene and phenoxathiin cation radicals to alkenes and alkynes

Polymerization of Vinyl Monomers Initiated by Thianthrene Cation Radical with Potential Biological Activity

Catalytic Aerobic Oxidation of Hydrazines into 2‐Tetrazenes

Contact Info

Product

Resources

About