Distribution of the products of benzhydryl bromide heterolysis in the presence of triphenylverdazyl in aprotic solvents

Serebryakov, Igor M.; Kryzhanovskaya, E. B.; Dzhurinskaya, S. S.

doi:10.1134/s1070363206050239

Cited by 1 publication

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References 2 publications

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“…The verdazyls 4 are reduced reversibly to leucoverdazyls 2 and are oxidized to verdazyl cations 5 and form complexes with benzene, benzoquinones, and other n-and π-acceptors [2-4, 7, 26, 29-33], making it possible to use them for the solution of many problems of organic chemistry, including the study of one-electron transfer processes. The verdazyl method (the Dvorko method) has been used successfully to study the kinetics and mechanisms of the monomolecular heterolysis of organohalogen compounds, including industrially employed compounds [7,34,35], although the principles of the method have undergone revision [36].…”

Section: 234-tetrahydro-1245-tetrazinesmentioning

confidence: 99%

Formazans in the synthesis of heterocycles. II. Synthesis of azines (Review)

Бузыкин

2010

Chem Heterocycl Comp

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The availability of various types of formazans, the prospects for their use in the synthesis of heterocycles, and the principles of the construction of various heterocyclic systems on the basis of the formazan fragment have already been discussed in general features in the first part of our review devoted to the synthesis of azoles on the formazans basis [1]. We will therefore only present a more detailed scheme of the possible paths to the formation of six-membered heterocyclic systems from formazans. As in the case of azoles, the principles of the construction of azine rings are based on the ability of the formazan fragment to enter completely or partially into the heterocycle that forms (Scheme 1) [2][3][4][5][6][7][8][9][10][11]. Most of the described paths (a-g in Scheme 1) involve intramolecular cyclization quite often without isolation of the precursor. There are only two examples of intermolecular [4+2] cycloaddition of formazans as 1,2,4-triazabuta-1,3-dienes with only one type of dienophile (path h) [12], since it has been demonstrated that the formation of 1,4-diaryl-3,6-bis(arylazo)-1,4-dihydro-1,2,4,5-tetrazines from 1,5-diaryl-3-chloroformazans (path i) is a two-step process and can be regarded as a variant of the intramolecular cyclization of path d (Scheme 1).The N-1 atom and one of the atoms of the substituents at the N-5 atom of the formazan fragment are most often involved in the intramolecular cyclization of formazans to azine derivatives according to a [6+0] scheme (paths a-c, described for the C and B atoms). In other cases the formation of the six-membered ring according to the [6+0] scheme results from nucleophilic substitution by a fragment of the meso substituent (from R 3 ) at the N-5 atom of the formazan fragment (paths d-f and, possibly, i). The cyclization of formazans with loss of one of the nitrogen atoms has only been described for cases of the formation of benzo-1,2,4-tria-zines (path h) [2-5, 10, 11].

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Section: 234-tetrahydro-1245-tetrazinesmentioning

confidence: 99%

Formazans in the synthesis of heterocycles. II. Synthesis of azines (Review)

Бузыкин

2010

Chem Heterocycl Comp

View full text Add to dashboard Cite

show abstract

Distribution of the products of benzhydryl bromide heterolysis in the presence of triphenylverdazyl in aprotic solvents

Cited by 1 publication

References 2 publications

Formazans in the synthesis of heterocycles. II. Synthesis of azines (Review)

Formazans in the synthesis of heterocycles. II. Synthesis of azines (Review)

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