Reactions of bishalomethylarenes with superoxide

Dao, Lê H.; Hopkinson, Alan C.; Lee‐Ruff, Edward; Rigaudy, J.

doi:10.1139/v77-534

Cited by 10 publications

(3 citation statements)

References 5 publications

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“…The latter polymerized rapidly at 20" in dilute solutions. This was no surprise as the known mono-endoperoxide 21 was also reported to be an unstable compound [8].…”

mentioning

confidence: 92%

Conformational Analysis of Endoperoxides Grafted onto Bicyclo[2.2.n]alkanes as a Test of the Rigidity of the Bicyclic Skeleton. Photo‐oxidation of [2.2.2] Hericene and 2,3,5,6‐Tetramethylidenebicyclo[2.2.n]alkanes

Birbaum

Vogel

1986

Helvetica Chimica Acta

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The photo-oxidation of [2.2.2]hericene (6) gave successively the endoperoxides 1 1 (9,10,11,12-tetramethylidene-4,S-dioxatricyclo[6.2.2.O2~7]dodec-2(7)-ene), the bis-endoperoxide 16 (1 5,16-dimethylidene-4,5,11,12-tetraoxatetracyclo[6.6.2.02~7.09~'4]hexadeca-2(7),9( 14)-diene), and the tris-endoperoxide 19 (4,5,11,12,17,18-hexaoxapentacyclo[6.6.6.02~7.09~'4.0'5~20]i~~~a-2(7),9( 14), 15 (20) with that reported for the ethylenetetracarbonitrile (TCNE) cycloadditions to the same polyenes. The rate-constant ratios k , / k , and k2/k3 for the three successive photo-oxidations of [2.2.2]hericene (6) did not differ significantly from unity, in contrast with the Diels-Alder additions of 6. Similarly, the rate-constant ratios k , / k , for the two successive photo-oxidations of tetraenes 7 and 8 were significantly smaller than those reported for the successive TCNE cycloadditions to 7 to 8. The endoperoxidc formations are not sensitive to the change in the exothermicity of the reactions but they are sensitive to the electronic properties (1P's)

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“…The latter polymerized rapidly at 20" in dilute solutions. This was no surprise as the known mono-endoperoxide 21 was also reported to be an unstable compound [8].…”

mentioning

confidence: 92%

Conformational Analysis of Endoperoxides Grafted onto Bicyclo[2.2.n]alkanes as a Test of the Rigidity of the Bicyclic Skeleton. Photo‐oxidation of [2.2.2] Hericene and 2,3,5,6‐Tetramethylidenebicyclo[2.2.n]alkanes

Birbaum

Vogel

1986

Helvetica Chimica Acta

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“…It should be noted that there are three known structural isomers of benzodioxane (BD): unstable 1,2-benzodioxane [30][31][32], 1,3-benzodioxane [33] and most stable 1,4-benzodioxane [34] (Figure 1). It is worth noting that the latest isomer, 1,4-benzodioxane (2,3-dihydro-1,4-benzodioxine), originally synthesized by German chemist Vorländer [35], possessed the highest chemical and thermal stability [36].…”

Section: Introductionmentioning

confidence: 99%

Convenient Preparation, Thermal Properties and X-ray Structure Determination of 2,3-Dihydro-5,6,7,8-tetranitro-1,4-benzodioxine (TNBD): A Promising High-Energy-Density Material

Šarlauskas

2024

IJMS

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2,3-dihydro-5,6,7,8-tetranitro-1,4-benzodioxine (TNBD), molecular formula = C8H4N4O10, is a completely nitrated aromatic ring 1,4-benzodioxane derivative. The convenient method of TNBD synthesis was developed (yield = 81%). The detailed structure of this compound was investigated by X-ray crystallography. The results of the thermal analysis (TG) obtained with twice re-crystallized material revealed the onset at 240 °C (partial sublimation started) and melting at 286 °C. The investigated material degraded completely at 290–329 °C. The experimental density of 1.85 g/cm3 of TNBD was determined by X-ray crystallography. The spectral properties of TNBD (NMR, FT-IR and Raman) were explored. The detonation properties of TNBD calculated by the EXPLO 5 code were slightly superior in comparison to standard high-energy material—tetryl (detonation velocity of TNBD—7727 m/s; detonation pressure—278 kbar; and tetryl—7570 m/s and 226.4 kbar at 1.614 g/cm3, or 260 kbar at higher density at 1.71 g/cm3. The obtained preliminary results might suggest TNBD can be a potential thermostable high-energy and -density material (HEDM).

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“…Althought mixed O,N-heterocycles, such as 1,2,5-, 1,2,4-and 1,3,4-oxadiazoles [16][17][18][19][20], as well as oxadiazole N-oxides (furoxans) [21][22][23][24][25][26] , are now amongst the most popular newly designed energetic compounds [27], derivatives of "pure" O-heterocycles as energetic materials have hardly been mentioned in scientific literature (except for unstable cyclic peroxides) [28]. 1,4-Benzodioxane (also known as 1,2-ethylenedioxybenzene, benzo-1,4-dioxane (old chemical names) or 2,3-dihydro-1,4-benzodioxin (new systematic name)) is one of many benzene annulated oxygen O-heterocycles [29].…”

Section: Introductionmentioning

confidence: 99%

Convenient Preparation, Thermal Properties and X-Ray Structure Determination of 2,3-Dihydro-5,6,7,8-tetranitro-1,4-benzodioxine (TNBD): a Promising High Energy Density Material (HEDM)

Šarlauskas

2024

Preprint

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: 2,3-dihydro-5,6,7,8-tetranitro-1,4-benzodioxine (TNBD), molecular formula =C8H4N4O10 is a completely nitrated in aromatic ring 1,4-benzodioxane derivative. The con-venient method of TNBD synthesis was developed (yield=81 %). The detailed structure of this compound has been investigated by X-ray crystallography. The results of differential thermal analysis (DTA) obtained with twice re-crystallized material showed onset at 247 and isoterm at 288 0C, with further total degradation at 300 0C. The experimental density 1,85 g/cm3 of TNBD was determined by X-ray crystallography. The spectral properties of TNBD (NMR, FT-IR, Ra-man) were explored. The detonation properties of TNBD calculated by EXPLO 5 code was slightly superior in comparison to standard high energy material - tetryl (detonation velocity of TNBD - 7727 m/s; detonation pressure - 278 kbar; tetryl – 7570 m/s and 226.4 kbar at 1.614 g/cm3, or 260 kbar at higher density - 1.71 g/cm3. The obtained preliminary results might suggest TNBD can be a potential thermostable high energy and density material (HEDM).

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Reactions of bishalomethylarenes with superoxide

Cited by 10 publications

References 5 publications

Conformational Analysis of Endoperoxides Grafted onto Bicyclo[2.2.n]alkanes as a Test of the Rigidity of the Bicyclic Skeleton. Photo‐oxidation of [2.2.2] Hericene and 2,3,5,6‐Tetramethylidenebicyclo[2.2.n]alkanes

Conformational Analysis of Endoperoxides Grafted onto Bicyclo[2.2.n]alkanes as a Test of the Rigidity of the Bicyclic Skeleton. Photo‐oxidation of [2.2.2] Hericene and 2,3,5,6‐Tetramethylidenebicyclo[2.2.n]alkanes

Convenient Preparation, Thermal Properties and X-ray Structure Determination of 2,3-Dihydro-5,6,7,8-tetranitro-1,4-benzodioxine (TNBD): A Promising High-Energy-Density Material

Convenient Preparation, Thermal Properties and X-Ray Structure Determination of 2,3-Dihydro-5,6,7,8-tetranitro-1,4-benzodioxine (TNBD): a Promising High Energy Density Material (HEDM)

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