JLM Gordon

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ChemInform Abstract: The Chlorination of Some 4‐Chloro‐2,6‐dimethylphenols. Some Addition Reactions of Substituted 4,6‐Dichloro‐2,6‐dimethylcyclohexa‐2,4‐ dienones.

ChemInform (1992)

JLM Gordon Michael P. Hartshorn RJ Martyn Ward T. Robinson G. J. WRIGHT

Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

10.1002/chin.199221119

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The Nitration of Tetrachlorocatechol and 3,4,6-Trichloro-5-methylcatechol. The Formation of 1-Hydroxycyclopent-3-enecarboxylic Acids

Australian Journal of Chemistry (1992)

J. L. CALVERT JLM Gordon MP Hartshorn W.T. Robinson GJ Wright

Reaction of tetrachlorocatechol (la) with nitric acid (d 1.48) gives the ring-contracted hydroxy dinitro acid (4), which was isolated as its ether solvate. Similar nitration of 3,4,6-trichloro-5-methylcatechol (lb) gives a mixture of stereoisomeric hydroxy dinitro acids (5), from which the methoxy methyl ester (8) can be isolated after methylation of the mixture with diazomethane. X-Ray crystal structure determinations are reported for the etherate of hydroxy dinitro acid (4) and the methoxy methyl ester (8).

Diazomethane

Biocatalysis

Nitric acid

10.1071/ch9920713

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The Mechanism and Stereochemistry of Chlorination of Some 2,4-Dichloro-6-methylphenols; X-Ray Crystal Structures of Some Polyhalo Ketones

Australian Journal of Chemistry (1994)

JLM Gordon MP Hartshorn RJ Martyn W.T. Robinson GJ Wright

The additions of chlorine to the 2,4,6-trichloro-5,6-dimethyl- (7a) and 2,4,6-trichloro-6-methyl- (7b) cyclohexa-2,4-dienones to give pentachlorocyclohexenones (8)-(11) are described. The stereochemistry of some of these additions has been determined from structural studies of the chlorination products of the 2,4-dibromophenols (12). X-Ray crystal structure determinations are reported for compounds (11b), (18), (20) and (23).

Biocatalysis

Quantum Chemistry

Chlorine atom

Crystal (programming language)

10.1071/ch9941071

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Citations (3)

The Chlorination of Some Substituted 2,4-Dimethylphenols

Australian Journal of Chemistry (1994)

JLM Gordon MP Hartshorn RJ Martyn A. J. Morgan W.T. Robinson

Chlorination reactions of 2-chloro-3,4,6-trimethylphenol (4), 2-chloro-4,6-dimethylphenol (5) and 3-chloro-2,4,6-trimethylphenol (6) are described. In acetic acid or acetic anhydride solution, chlorinations yield predominantly the corresponding 4-chlorocyclohexa-2,5-dienones (8), (17a) and (29), but in carbon tetrachloride containing pyridine products are formed which result from the modification of the 4-methyl group in each substrate. X-Ray crystal structure analyses are reported for compounds (7), (14), (28) and (31).

Biocatalysis

10.1071/ch9940289

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Citations (3)

The Reactions of Some Substituted 2-Hydroxybenzonitriles With Nitrogen Dioxide: X-Ray Structures of 2-Cyano-t-6-hydroxy-3,4,5,6-tetramethyl-r-4,t-5-dinitrocyclohex- 2-enone, 2-Cyano-3,4,5,6-tetramethyl-r-4,t-5,t-6-trinitrocyclohex-2-enone and 2-Cyano-c-6-h-4,6-dimethyl-r-4,c-5-dinitrocyclohex-2-enone

Australian Journal of Chemistry (1990)

JLM Gordon MP Hartshorn W.T. Robinson C. W. SIES B. A. WELLS

Reaction of 2-hydroxy-3,4,5,6-tetramethylbenzonitrile (1c) with nitrogen dioxide gives predominantly the 4,5,6-trinitrocyclohex-2-enones (9) and (10a,b), with lower yields of the 4-nitro dienone (5a) and the 6-hydroxy-4,5-dinitrocyclohex-2-enone (6). Reaction of 2-hydroxy-3,5-dimethylbenzonitrile (2b) with nitrogen dioxide gave the C4-epimeric 6-hydroxy-4,5-dinitrocyclohex-2-enones (11) and (12). Reaction of 2-hydroxy-3,5,6-trimethyl- benzene-1,4-dicarbonitrile (4) with nitrogen dioxide gave the 4-hydroxy dienone (15) and the 6-hydroxy dienone (16). X-Ray structure determinations are reported for compounds (6), (9) and (11).

Enone

Nitrogen dioxide

Biocatalysis

10.1071/ch9900579

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Citations (2)

The Chlorination of Some 4-Chloro-2,6-dimethylphenols. Some Addition Reactions of Substituted 4,6-Dichloro-2,6-dimethylcyclohexa-2,4-dienones

Australian Journal of Chemistry (1992)

JLM Gordon MP Hartshorn RJ Martyn W.T. Robinson GJ Wright

Reactions of 4,6-dichlorocyclohexa-2,4dienone (4c) with chlorine in acetic acid and with chlorine in acetic acid containing sodium acetate are described, as are the corresponding reactions for a mixture of the 4,5,6-trichloro-(4b) and 3,4,6-trichloro-cyclohexa-2,4-dienone (5b). X-Ray crystal structures are reported for compounds (3b), (7), (9b), (11) and (13).

Biocatalysis

Sodium acetate

Chlorine atom

10.1071/ch9920337

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Citations (2)

ChemInform Abstract: Chlorination of Some Substituted 2,4‐Dimethylphenols.

ChemInform (1994)

JLM Gordon Michael P. Hartshorn RJ Martyn A. J. Morgan Ward T. Robinson

10.1002/chin.199425090

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Ipso attack of aromatic systems

JLM Gordon

10.26021/8170

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Citations (1)

ChemInform Abstract: Nitration of Tetrachlorocatechol and 3,4,6‐Trichloro‐5‐methylcatechol. Formation of 1‐Hydroxycyclopent‐3‐enecarboxylic Acids.

ChemInform (1992)

J. L. CALVERT JLM Gordon Michael P. Hartshorn Ward T. Robinson G. J. WRIGHT

10.1002/chin.199230109

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

Australian Journal of Chemistry (1994)

JLM Gordon MP Hartshorn RJ Martyn W.T. Robinson GJ Wright

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).

Biocatalysis

Chlorine atom

10.1071/ch9940279

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Citations (3)