reactions of 2-t-Butyl-4,6-dimethylphenol, 2,4-Di-t-butyl-6-methylphenol and 2,4,6-Tri-t-butylphenol with Nitrogen Dioxide

1985 ◽  
Vol 38 (1) ◽  
pp. 161 ◽  
Author(s):  
MP Hartshorn ◽  
WT Robinson ◽  
KH Sutton ◽  
J Vaughan
Keyword(s):  
Nitrogen Dioxide ◽  
Crystal Structures ◽  
Similar Reaction ◽  
X Ray

Reaction of 2-t-butyl-4,6-dimethylphenol(10) with nitrogen dioxide in benzene gives the C4-epimeric 4,5,6-trinitrocyclohex-2-enones (13) and (14). In contrast, similar reaction of 2,4-di-t-butyl-6-methyl-phenol (11) gives substituted cyclohex-3-enones, 2,5,6-trinitro ketones (20)- (23), 2-hydroxy-5,6-dinitro ketones (27) and (28) and the 6-hydroxy- 2,5-dinitro ketone (29). Reaction of 2,4,6-tri-t-butylphenol (12) with nitrogen dioxide gives initially the 4-nitro dienone (35), but de-t- butylated products (36) and (37) are formed in long-term reactions. X- ray crystal structures are reported for compounds (13),(14),(21),(22), (23), (27), (28) and (29).

Reactions of 3,4,5-Trimethylbiphenyl and 2,3,4-Trimethylbiphenyl With Nitrogen Dioxide

1990 ◽  
Vol 43 (9) ◽  
pp. 1519 ◽  
Author(s):  
MP Hartshorn ◽  
MC Judd ◽  
RJ Martyn ◽  
WT Robinson ◽  
GJ Wright ◽  
...  
Keyword(s):  
Nitrogen Dioxide ◽  
Crystal Structures ◽  
Nitroaromatic Compounds ◽  
Similar Reaction ◽  
X Ray ◽  
Nitrate Esters ◽  
Elimination Mechanism

Reaction of 3,4,5-trimethylbiphenyl (1) with nitrogen dioxide gives four mononitro compounds (3)-(6) and three dinitro compounds (7)-(9). Similar reaction of 2,3,4-trimethylbiphenyl (2) gives three nitroaromatic compounds (11)-(13), three nitrate esters (14)-(16), and two nitro dienones (17) and (18). Dinitro dienone (17) rearranges in solution to give the corresponding hydroxy nitro dienone (19). The differences between the two sets of products are discussed, and an addition-elimination mechanism is proposed for the mode of formation of the nitro dienones (17) and (18). X-Ray crystal structures are reported for compounds (4) and (19).

Combination of Pyridinium and Isoquinolinium Ylides with Phenylisocyanate and Isothiocyanates: Synthesis, Characterisation, and X-Ray Crystal Structures of Mesoionic Monosubstituted 3-Oxo-Propanamides or Thioamides

2015 ◽  
Vol 68 (10) ◽  
pp. 1577
Author(s):  
Mohammad Seifi ◽  
S. Yousef Ebrahimipour ◽  
Jim Simpson ◽  
Michal Dusek ◽  
Vaclav Eigner ◽  
...  
Keyword(s):  
Single Crystal ◽  
Crystal Structures ◽  
Similar Reaction ◽  
X Ray ◽  
Pyridinium Ylides

Pyridinium ylides derived from 2-bromoacetophenone or methyl bromoacetate have been reacted with phenylisocyanate, phenyl- or methylisothiocyanate to afford mesoionic monosubstituted 3-oxo-propanamides or thioamides, via self-protonation of the intermediate N-anion. A similar reaction under the same conditions of isoquinolinium ylides with phenylisocyanate or phenyisothiocyante also produced the corresponding mesoionic compounds. In order to establish the exact structure of the mesoionic compounds, single crystal X-ray structures were obtained for three of the pyridinium ylides.

Nitration of 2,3,4,6-Tetramethylphenol and 1,2,3,5-Tetramethylbenzene

1985 ◽  
Vol 38 (4) ◽  
pp. 587 ◽  
Author(s):  
MP Hartshorn ◽  
JM Readman ◽  
WT Robinson ◽  
J Vaughan
Keyword(s):  
Nitric Acid ◽  
Nitrogen Dioxide ◽  
Crystal Structures ◽  
Side Chain ◽  
X Ray ◽  
Fuming Nitric Acid

Nitration of 1,2,3,5-tetramethylbenzene (2a) with fuming nitric acid gives the tetramethylnitrobenzene (22), products of side-chain modification (23)-(27), the rearranged 6,6-dimethylcyclohexenones (8), (28), (29) and (30), and 2,3,4,6-tetramethyl ketone derivatives (10)- (13), (31) and (32). Reaction of 2,3,4,6-tetramethylphenol (7) with nitrogen dioxide gives the hydroxy dinitro ketone (9) in addition to the trinitrocyclohexenones (11)-(14) and (19). X-ray crystal structures are reported for compounds (11), (19), (28), (29), (30) and (32). 1H n.m.r ./stereochemistry correlations are reported for some 2,5-dinitro- and 2,5,6-trinitro-cyclohex-3-enones.

The nitration of pentamethylphenol

1984 ◽  
Vol 37 (7) ◽  
pp. 1489 ◽  
Author(s):  
MP Hartshorn ◽  
WT Robinson ◽  
J Vaughan ◽  
JM White ◽  
AR Whyte
Keyword(s):  
Nitric Acid ◽  
Nitrogen Dioxide ◽  
Crystal Structures ◽  
X Ray ◽  
Fuming Nitric Acid

Nitration of pentamethylphenol (1) with nitrogen dioxide in benzene gives the four possible 2,5,6-trinitrocyclohex-3-enones (6), (7), (8) and (9), three 4,5,6-trinitrocyclohex-2-enones (10), (11) and [(12) or (13)], the 2-hydroxy-5,6-dinitrocyclohex-3-enone (14), quinone (17) and the 4-nitro dienone (3). The fuming nitric acid nitration of pentamethylphenol (1) for 90 h gives most of these products, except that 4-nitratomethyl-2,5,6-trinitrocyclohex-3-eones (21), (22), (23) and (24) are isolated. X-ray crystal structures are reported for compounds (6), (7), (8), (10), (11), (14) and (21).

The Chlorination of 2-t-Butyl-4-chloro-6-methylphenol. Some Reactions of Chlorine and Nitrogen Dioxide With 6-Chlorocyclohexa-2,4-dienones Derived From 2-t-Butyl-4-chloro-6-methylphenol

1992 ◽  
Vol 45 (4) ◽  
pp. 721 ◽  
Author(s):  
MP Hartshorn ◽  
AD Roddick ◽  
PJ Steel ◽  
GJ Wright
Keyword(s):  
Nitrogen Dioxide ◽  
Crystal Structures ◽  
X Ray

Chlorinations of 2-t-butyl-4-chloro-6-methylphenol(10) and of the mixture of 4,6-dichlorocyclo-hexa-2,ddienones (11) and (12) give the tetrachloro ketones (13)-(15). Reaction of the dichlorocyclohexa-2,4-dienone mixture with nitrogen dioxide gives predominantly dichloro dinitro ketones (17) which rearrange on chromatography to yield the hydroxy dienone (21). X-Ray crystal structures are reported for compounds (13)-(15), (20) and (21).

Reactions of 2,6-Di-t-butyl-4-methylphenol with nitrogen dioxide; X-ray crystal structures of 2,6-Di-t-butyl-c-6-hydroxy-4-methyl-r-4,c-5-dinitrocyclohex-2-enone and 2,6-Di-t-butyl-4-methyl-r-4,c-5,c-6-trinitrocyclohex-2-enone

1983 ◽  
Vol 36 (11) ◽  
pp. 2339 ◽  
Author(s):  
MP Hartshorn ◽  
KH Sutton ◽  
J Vaughan
Keyword(s):  
Nitrogen Dioxide ◽  
Crystal Structures ◽  
X Ray

Reaction of 2,6-di-t-butyl-4-methylphenol (6) with nitrogen dioxide in benzene gives the trinitro ketone (11), but in cyclohexane gives both trinitro ketone (11) and the hydroxy dinitro ketone (12),in addition to the 4-nitro dienone (10). Some reactions and X-ray crystal structures of compounds (11) and (12) are described.

The Mechanism and Stereochemistry of Chlorination of 2,4-Dichloro-3,,5,6-trimethylphenol and 2,4-Dichloro-3,6-dimethylphenol

1994 ◽  
Vol 47 (2) ◽  
pp. 279 ◽  
Author(s):  
JLM Gordon ◽  
MP Hartshorn ◽  
RJ Martyn ◽  
WT Robinson ◽  
GJ Wright
Keyword(s):  
Crystal Structures ◽  
Similar Reaction ◽  
Electrophilic Attack ◽  
X Ray

Electrophilic attack of chlorine on 2,4,6-trichloro-3,5,6-trimethylcyclohexa-2,4-dienone (2a) gives the trans-pentachloro ketones (3a) and (4a), while similar reaction of 2,4,6-trichloro-3,6-dimethylcyclohexa-2,4-dienone (2b) gives the trans- pentachloro ketones (3b) and (4b), resulting from 2,5- and 4,5-addition of chlorine. The probable stereochemistry of chlorine addition in ketones (3b) and (4b) is determined by chlorination of 2,4-dibromo-3,6-dimethylphenol (6). X-Ray crystal structures are reported for compounds (3a,b), (7) and (8).

Distibylation of Acetylenes with Ph2Sb–SbPh2: Synthesis, Crystal Structures and Phosphorescence Properties of Bis(diphenylstibyl)ethenes

2014 ◽  
Vol 69 (11-12) ◽  
pp. 1181-1187
Author(s):  
Joji Ohshita ◽  
Toshiyuki Tsuchida ◽  
Kazuya Murakami ◽  
Yousuke Ooyama ◽  
Takayuki Nakanishi ◽  
...  
Keyword(s):  
Optical Properties ◽  
Solid State ◽  
Low Temperature ◽  
Crystal Structures ◽  
Uv Absorption ◽  
Similar Reaction ◽  
Photoluminescence Spectra ◽  
X Ray Diffraction ◽  
X Ray

Abstract Treatment of tetraphenyldistibine (1) with terminal arylacetylenes, XC6H5C≡CH (2a-c, X=H, F, OMe), gave the corresponding anti-addition products (E)-aryl-1,2-bis(diphenylstibyl)ethenes 3a-c in 11 - 17% yields. A similar reaction of 1 with 1,4-diphenylbutadiyne provided (E)-1,4-diphenyl- 1,2-bis(diphenylstibyl)but-1-en-3-yne (3d) in 28% yield. X-Ray diffraction studies on crystals of 3a, 3b and 3d revealed a congested configuration around the ethylene core. The optical properties of the adducts 3a-d were examined by measuring UV absorption and photoluminescence spectra. Interestingly, 3d showed phosphorescence in the solid state, which was enhanced at low temperature.

scholarly journals Synthesis and crystal structures of two new tin bis(carboranylamidinate) complexes

2017 ◽  
Vol 73 (10) ◽  
pp. 1443-1448 ◽  
Author(s):  
Nicole Harmgarth ◽  
Phil Liebing ◽  
Philipp Hillebrand ◽  
Sabine Busse ◽  
Frank T. Edelmann
Keyword(s):  
Single Crystal ◽  
Crystal Structures ◽  
Structure Analysis ◽  
Lone Pair ◽  
Main Reaction ◽  
Similar Reaction ◽  
Main Reaction Product ◽  
X Ray ◽  
Trigonal Bipyramidal Coordination ◽  
Trigonal Bipyramidal

Reaction of 2 equiv. of the lithium carboranylamidinate Li[o-(C2H10B10)C(NCy)(NHCy)] with SnCl2in THF afforded the stannylene compound bis(N,N′-dicyclohexylamidinatocarboranate)tin(II), SnII[o-(C2H10B10)C(NCy)(NHCy)]2(1). A similar reaction of SnCl4with 2 equiv. of Li[o-(C2H10B10)C(NiPr)(NHiPr)] unexpectedly afforded the known solvated pentachloridostannate(IV) salt [Li(THF)4][SnCl5(THF)] as the main reaction product. Small amounts of the new chlorido-tin(IV) bis(carboranylamidinate) bis(N,N′-diisopropylamidinatocarboranate)chloridotin(IV), SnIVCl[o-(C2H10B10)C(NiPr)(NHiPr)][o-(C2H10B10)C(NiPr)2] (2), were isolated as a by-product. Single-crystal X-ray structure analysis revealed aκC,κN-chelating coordination of the carboranylamidinate ligands in both1and2. The Sn atom in1adopts a pseudo-trigonal–bipyramidal coordination under participation of a stereoactive lone pair. In2, a trigonal–bipyramidal coordination of Sn is completed by a chlorido ligand.

The Reaction of 2,3,5,6-Tetramethyl-4-nitrophenol with Nitrogen Dioxide

1985 ◽  
Vol 38 (1) ◽  
pp. 145 ◽  
Author(s):  
MP Hartshorn ◽  
WT Robinson ◽  
JWJM Vaughan
Keyword(s):  
Nitrogen Dioxide ◽  
Crystal Structures ◽  
X Ray

Reaction of 2,3,5,6-tetramethyl-4-nitrophenol (21) with nitrogen dioxide in benzene gives the four isomeric 2,4,5,6-tetranitrocyclohex- 3-enones (24)-(27), 2-hydroxy-4,5,6-trinitrocyclohex-3-enone (31), the C2-epimeric 6-hydroxy-2,4,5-trinitrocyclohex-3-enones (32) and (36) and the 2,6-dihydroxy-4,5-dinitrocyclohex-3-enone (33). X-ray crystal structures are reported for compounds (24), (25), (31), (32), (36) and the cyclopentenediol (37).

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