A Modification of the Clemmensen Method of Reduction<sup>1</sup>

Martin, E. L.

doi:10.1021/ja01299a038

Cited by 119 publications

(40 citation statements)

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“…25 Cyclization of 6 by treatment of polyphosphoric acid (PPA) gave 26 7-substituted 3,4-dihydronaphthalen-1(2H)-one 7a, 7b that were converted to the pinacol 8 (1,2,3,4-tetrahydro-1-(1,2,3,4-tetrahydro-1-hydroxynaphthalen-1-yl)naphthalen-1-ol 8a and its derivative 8b) with amalgamated aluminum foil in alcohol-benzene according to the procedure described by Newman. 27 The pinacol 8 was isolated as a mixture of crystals.…”

Section: Resultsmentioning

confidence: 99%

The conformational diastereomers of 7-substituted-(8Z)-8-chloro-6,7-dihydro-9-(1,2-dihydro-6-R-naphthalen-4-yl)-2-R-5H-benzo[7]annulene, the question of atropisomerism versus ring inversion

Ranjbar¹,

Roshan²

2010

Arkivoc

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Conformational diastereomers of 7-substituted-(8Z)-8-chloro-6,7-dihydro-9-(1,2-dihydronaphthalen-4-yl)-5H-benzo [7]annulene 1 are observed at room temperature in solution. Two conformational processes are possible in 1, i.e. atropisomerism around the sp 2 -sp 2 pivot bond and ring inversion of cycloheptadiene moiety which together provide four minima structures. The 3 J calculation by Haasnoot equation on optimized structures is accordance with the 7-substituents in pseudo equatorial (exo) position in both forms. The barrier to conformational process is determined by dynamic 1 H-NMR spectroscopy to be ∆G ≠ (365K) =74.5±0.5 kJ/mol. Solvent dependent populations of the two forms are studied in DMSO-d 6 and CDCl 3 , the population ratio is not sensitive to solvent polarity.

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Section: Resultsmentioning

confidence: 99%

The conformational diastereomers of 7-substituted-(8Z)-8-chloro-6,7-dihydro-9-(1,2-dihydro-6-R-naphthalen-4-yl)-2-R-5H-benzo[7]annulene, the question of atropisomerism versus ring inversion

Ranjbar¹,

Roshan²

2010

Arkivoc

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“…$-Ethylphenol and 9-n-propylphenol were prepared by the Martin modification (12,21) of the Cleinmenseil reduction of purified p-l~yclroxyacetopl~en-one and p-hydroxypropiophenone, respectively. p-n-Butylphenol was prepared by sulphonatiilg the pure hydrocarboil (21).…”

Section: Methodsmentioning

confidence: 99%

Influence of the Number of Carbon Atoms of the Alkyl Group on Polymerization and Properties of Para-Alkylphenol–formaldehyde Polymers

Rosenthal¹,

Lederer²,

Gilson³

1956

Can. J. Chem.

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The polymerization (in organic media) of p-cresol-formaldehyde has been i~lvestigated in sealed t~~b e s and in open systems. A series of almost colorless p-alkylphenol-forn~aldehyde polymers, prepared in sealed t~~b e s , was s t~~d i e d to determine the influence of the number of carbon atoms of the substituting aIky1 group on the polymerization process and on the properties of the polymers. Infrared spectra and che~nical analyses of the original and heat-treated poly~ners ' were correlated with the structures of the polymers.Para-all

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“…The parent 4-oxoacid namely 4-oxo-4-phenylbutanoic acid (S1) and the phenyl substituted 4-oxoacids (S2-S7) were prepared by Friedel-Crafts acylation of the substituted benzene with succinic anhydride [7][8][9][10][11]. Nitration of oxoacids has been performed under mild conditions to prepare nitro compounds.…”

Section: Experimental Section Materialsmentioning

confidence: 99%

Kinetics and mechanism of oxidation of 4-oxoacids by N-bromosuccinimide in aqueous acetic acid medium

Farook¹

2006

JICS

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Kinetics and mechanism of oxidation of substituted and unsubstituted 4-oxoacids (S) by N-bromosuccinimide (NBS) in aqueous acetic acid medium have been studied potentiometrically. The reaction follows first-order kinetics, each in 4-oxoacids, NBS and H + . The effect of changes in the electronic nature of the substrate reveals that there is a development of positive charge in the transition state. Based on the kinetic results and the product analysis, a suitable mechanism has been proposed for the reaction of NBS with 4-oxoacids.

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A Modification of the Clemmensen Method of Reduction¹

Cited by 119 publications

References 0 publications

The conformational diastereomers of 7-substituted-(8Z)-8-chloro-6,7-dihydro-9-(1,2-dihydro-6-R-naphthalen-4-yl)-2-R-5H-benzo[7]annulene, the question of atropisomerism versus ring inversion

The conformational diastereomers of 7-substituted-(8Z)-8-chloro-6,7-dihydro-9-(1,2-dihydro-6-R-naphthalen-4-yl)-2-R-5H-benzo[7]annulene, the question of atropisomerism versus ring inversion

Influence of the Number of Carbon Atoms of the Alkyl Group on Polymerization and Properties of Para-Alkylphenol–formaldehyde Polymers

Kinetics and mechanism of oxidation of 4-oxoacids by N-bromosuccinimide in aqueous acetic acid medium

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A Modification of the Clemmensen Method of Reduction1

Cited by 119 publications

References 0 publications

The conformational diastereomers of 7-substituted-(8Z)-8-chloro-6,7-dihydro-9-(1,2-dihydro-6-R-naphthalen-4-yl)-2-R-5H-benzo[7]annulene, the question of atropisomerism versus ring inversion

The conformational diastereomers of 7-substituted-(8Z)-8-chloro-6,7-dihydro-9-(1,2-dihydro-6-R-naphthalen-4-yl)-2-R-5H-benzo[7]annulene, the question of atropisomerism versus ring inversion

Influence of the Number of Carbon Atoms of the Alkyl Group on Polymerization and Properties of Para-Alkylphenol–formaldehyde Polymers

Kinetics and mechanism of oxidation of 4-oxoacids by N-bromosuccinimide in aqueous acetic acid medium

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A Modification of the Clemmensen Method of Reduction¹