THE <i>C</i>- AND <i>O</i>-BENZYLATION OF <scp>L</scp>-ASCORBIC ACID

Jackson, K. G. A.; Jones, J. K. N.

doi:10.1139/v65-060

Cited by 31 publications

(11 citation statements)

References 10 publications

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“…Thermally stable (heat-resistant) explosives are particularly interesting, becauset hey are stablea tt he high temperatures encounteredi nd rilling deep oil wells (e.g.,t hermally stable perforators) or in space exploration (e.g.,i na chieving stage separation in space rockets). [1] In this area, the following explosives have received special attention:1,3,5-triamino-2,4,6-trinitrobenzene (TATB), 2,2',4,4',6,, and 2,6bis(picrylamino)-3,5-dinitropyridine (PYX),s hown in Figure 1.…”

Section: Introductionmentioning

confidence: 99%

“…In 1888, Jacksona nd Wing prepared TATB by the reactiono f 1,3,5-tribromo-2,4,6-trinitrobenzene with ammonia,y ielding TATB as ap aley ellow solid. [2] TATB shows ah igh theoretical maximum density( 1 TMD = 1.93 gcm À3 ) [3] and has ah igh thermal stability( 310 8C). [4] In addition, TATB has ah igh Chapman-Jouguet (C-J) detonation velocity and pressure (D C-J = 7.66 km s À1 , P C-J = 28.7 GPa at ad ensity of 1.854 gcm À3 ;c ylinder test).…”

Section: Introductionmentioning

confidence: 99%

“…[8] It could be concluded that initiation of small TATB charges by aw eak initiatorc auses al ow reactione xtent at the Chapman-Jouguet plane and resultsi nl ow-order detonation. 2,2',4,4',6, was prepared by Shipp through the reactiono f2 ,4,6-trinitrobenzylc hloride with an alcoholic potassium hydroxide solution. [9] HNS has only am oderately high theoretical maximum density (1 TMD = 1.745 gcm À3 ) [10] and melts with subsequent decompositiona t3 18 8C.…”

Section: Introductionmentioning

confidence: 99%

“…[6] The search for explosives that are thermally more stable than HNS, but with lower sensitivities and better performances is an ongoingp rocess in many research groupsw orldwide. The other interestingt hermallys table explosives are:3 ,3'-di- 2',4,4',6,;c)2,6-bis(picrylamino)-3,5-dinitropyridine(PYX). , [15] 2,6-diamino-3,5-dinitropyrazine-1-oxide (LLM-105), [16] tetraazapentalenes [1,3,7,9-tetranitro-6H-benzotriazolo[2,1-a]benzotriazol-5-ium inner salt (Z-TACOT), [17] 2,4,8,10-tetranitro-5H-benzotriazolo[1,2-a]benzotriazol-6-ium inner salt (T-TACOT), [17c] and 2,4,8,2':4,5] [1,2,3]-triazolo [1,2-a]benzotriazol-6-ium inner salt (BPTAP) [18] ], 2,2',2'',4,4',4'',6,6',, [19] and 2,6-bis(picrylamino)-3,5-dinitropyridine(PYX).…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Investigation of 2,6‐Bis(picrylamino)‐3,5‐dinitro‐pyridine (PYX) and Its Salts

Klapötke

Stierstorfer

Weyrauther

et al. 2016

Chemistry A European J

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2,6-Bis(picrylamino)pyridine (1; pre-PYX) and 2,6-bis(picrylamino)-3,5-dinitropyridine (2; PYX) were synthesized using an improved literature method. Compounds 1 and 2 were reinvestigated in detail and the X-ray structures (1: ρ=1.698 g cm(-3) at 173 K; 2: ρ=1.757 g cm(-3) at 298 K) are given. The reactions of 2 with different bases, such as alkali metal hydroxides (sodium, potassium, rubidium, cesium), and N-bases (ammonia, hydrazine, hydroxylamine, guanidinium carbonate, aminoguanidine bicarbonate) are reported, as well as metathesis reactions producing energetic salts. Several energetic compounds were synthesized and characterized for the first time using vibrational (IR, Raman) and multinuclear NMR spectroscopy, mass spectrometry, elemental analysis, and DSC. The crystal structures of four energetic salts were determined using low temperature single-crystal X-ray diffraction. Heats of formation for the metal-free species were calculated using the Gaussian 09 software. Detonation parameters were estimated using the EXPLO5 program. The sensitivities towards impact, friction, and electrostatic discharge were also determined.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis and Investigation of 2,6‐Bis(picrylamino)‐3,5‐dinitro‐pyridine (PYX) and Its Salts

Klapötke

Stierstorfer

Weyrauther

et al. 2016

Chemistry A European J

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“…This degradation was proven b y the spectral evidence that the products had lost the lactone functionality. Degradation of the structurally related 2-C-benzyl ascorbic acid was reported earlier (5).…”

Section: Resultsmentioning

confidence: 66%

The Michael adduct of L-ascorbic acid to methyl vinyl ketone: its remarkable self-condensation and other reactions

Arnold¹,

Fodor²,

George³

et al. 1987

Can. J. Chem.

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. J. Chem. 65, 131 (1987).The structure of the Michael adduct of L-ascorbic acid (1) to methyl vinyl ketone was established as 2-(3-oxobuty1)-3-0x0-L-gulonolactone(3,6)hemiketal (3). In aqueous solution 3 is prone to undergo base-or acid-promoted degradations. I-(2-Fury])-l,4-pentanedione was isolated from the acidic product mixture. Under strictly anhydrous acid-catalyzed conditions, if a suitable nucleophile like ethanol is present, the tricyclic ethyl ketal6b forms. In the absence of a nucleophile, the unexpected self-condensation of 3 occurs leading to cyclo-trimer 7, the structure of which was established by X-ray crystallography. Trimer 7, held together via ketal bridges, is converted quantitatively into the tricyclic methyl ketal6a in methanolic hydrogen chloride. Mechanisms are proposed for the formation of 6 a and b or 7.REGINA ARNOLD, GABOR FODOR, CLIFFORD GEORGE et ISABELLA KARLE. Can. J. Chem. 65, 131 (1987) On a Ctabli que le produit d'addition de Michael de I'acide L-ascorbique (1) sur la methyl vinyl cCtone est le (0x0-3 buty1)-2 0x0-3 L-gulonolactone(3,6)hCrnicCtal (3). En solution aqueuse, le compost 3 est sujet i subir des dtgradations sous 1 'influence tant des acides que des bases. On a isolk la (furyl-2)-l pentanedione-2,4 du mklange des produits obtenus en milieu acide. En milieu acide strictement anhydre et en presence d'un nuclkophile approprik, cornrne l'kthanol, il se forme 1'Cthyl cCtal tricyclique 6b. En l'absence d'un nuclCophile, il se produit une auto-condensation surprenante du composC 3 qui conduit au cyclo-trimere7 dont la structure a Ctk Ctablie par diffraction des rayons-X. Sous l'influence du chlorure d'hydrogkne en milieu mkthanolique, le trimkre 7, qui est retenu ensemble par des ponts cktals, se transforme quantitativernent en methyl cktal tricyclique 6a. On propose des mkcanismes pour la formation des cornposks 6a et b ou du composk 7.[Traduit par la revue]

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