The Nitration of Methyl α-Naphthoate and Related Compounds<sup>1</sup>

Koelsch, C. F.; Hoffman, D. O.

doi:10.1021/ja01245a506

Cited by 3 publications

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“…Methyl 5-nitronaphthalene-1-carboxylate (9): light yellow crystals; mp 107−108 °C (lit . mp 107−109 °C); NMR δ H (CDCl 3 ) 4.04 (3H, s, CH 3 ), 7.67−7.77 (2H, m), 8.21 (1H, d, J = = 7.6), 8.31 (1H, d, J = 7.6), 8.68 (1H, d, J = 9.2), 9.27 (1H, d, J = 9.2); IR ν max (KBr)/cm -1 1721 (CO), 1516 (NO 2 ), 1339 (NO 2 ), 1277, 1154, 1059, 791, 768; MS m / z (CI) 232 (38, M + + 1), 202 (100).…”

Section: Methodsmentioning

confidence: 99%

Nonacid Nitration of Benzenedicarboxylic and Naphthalenecarboxylic Acid Esters

Nose

Suzuki

2001

J. Org. Chem.

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When treated with nitrogen dioxide in the presence of ozone and a catalytic amount of iron(III) chloride in inert organic solvent at -10 to +5 degrees C, benzenedicarboxylic acid diesters 1, 4, and 6 underwent smooth nitration to give the corresponding mononitro derivatives 2/3, 5, and 7, respectively, in good yield (kyodai nitration). Naphthalenecarboxylic acid esters 8 and 11 and naphthalene-1,8-dicarboxylic acid diester 16 were similarly nitrated in the absence of catalyst to give the expected nitro compounds 9/10, 12-15, and 17-22, respectively. Different from conventional nitration based on the combined use of concentrated nitric and sulfuric acids, no hydrolytic cleavage of the ester function was observed under these conditions. The isomer distribution has been determined for the nitration of naphthalenecarboxylic acid esters 8, 11, and 16, and spectral data were collected for less common nitro derivatives. A unique changeover of the orientation mode observed in the kyodai nitration of diester 16, from the initial exclusive meta to the final meta/para, has been discussed in terms of the competition between the electrophilic substitution process involving the nitronium ion (NO2+) and the addition-elimination sequence involving the nitrogen trioxide radical (*NO3).

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Section: Methodsmentioning

confidence: 99%

Nonacid Nitration of Benzenedicarboxylic and Naphthalenecarboxylic Acid Esters

Nose

Suzuki

2001

J. Org. Chem.

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“…Nitration of 1-naphthoic acid and separation from molecule, forming an incipient ion-pair 24). the 5-substituted isomer gave 8-nitro-1-naphthoic acid (27). The halogenation of the mercurated complex of…”

Section: ' Brmentioning

confidence: 99%

The transmission of polar effects. Part X. The esterification with diazodiphenyl-methane and the ionization of 9-substituted 10-anthroic and 8-substituted 1-naphthoic acids

Bowden¹,

Parkin²

1969

Can. J. Chem.

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The rate coefficients for the reaction with diazodiphenylmethane in methanol, ethanol, isopropyl alcohol, t-butyl alcohol, 2-methoxyetl1anol, 2-11-butoxpetlianol, and ethyl acetate at 30' and the pK, values in 80% 2-n-butoxyethanol-water of a series of 9-substit~~ted 10-anthroic and 8-substituted 1-naphtlioic acids have been determined. The effect of substitution has been analyzed by linear free energy relations. The variation in the susceptibilities of the systems to polar substituent effects \\.it11 the medium are examined. The occurrence of reversed dipolar substituent effects in the reactions of the I ,S-naphthoic acids is detected. The inlplications of the results for the inductive and field effect models for the transmission of polar effects are discussed.

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