The Alkylation of Benzene in the Presence of Acid Catalysts

Burwell, Robert L.; Archer, S.

doi:10.1021/ja01257a005

Cited by 28 publications

(11 citation statements)

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“…One of the most critical steps in the synthesis of 2 was the alkylation of compound 7 with alcohol 6. Even though the alkylation or acylation of aromatic compounds with alcohols and carboxylic acids, respectively, in the presence of polyacids is well described in the literature [17], the reaction of 6 with 7 might fail by leading to polymerization because of the benzyl bromide 7. Furthermore, alcohol 6 could have reacted with 7 at either C(2) or C(6).…”

mentioning

confidence: 99%

Total Synthesis of the Biologically Active, Naturally Occurring 3,4‐Dibromo‐5‐[2‐bromo‐3,4‐dihydroxy‐6‐(methoxymethyl)benzyl]benzene‐1,2‐diol and Regioselective O‐Demethylation of Aryl Methyl Ethers

Akbaba

Balaydın

Goksu

et al. 2010

Helvetica Chimica Acta

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.tr) 3,4-Dibromo-5-[2-bromo-3,4-dihydroxy-6-(methoxymethyl)benzyl]benzene-1,2-diol (2), a natural product, has been synthesized for the first time starting from (3-bromo-4,5-dimethoxyphenyl)methanol (5) in five steps and with an overall yield of 34%. The reaction of some methoxymethyl-substituted aryl methyl ethers with BBr 3 , followed by the addition of MeOH, afforded the corresponding methoxymethyl-substituted arylphenols in high yields.

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mentioning

confidence: 99%

Total Synthesis of the Biologically Active, Naturally Occurring 3,4‐Dibromo‐5‐[2‐bromo‐3,4‐dihydroxy‐6‐(methoxymethyl)benzyl]benzene‐1,2‐diol and Regioselective O‐Demethylation of Aryl Methyl Ethers

Akbaba

Balaydın

Goksu

et al. 2010

Helvetica Chimica Acta

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“…Equally, sulphation of alkan-2-ols with H2SO4 leads to some shift of the ester sulphate group towards the centre of the chain. These shifts are not totally unexpected, even during sulphation at low temperatures, in the light of the reactions possible between secondary alcohols and H2SO4 (Burwell, 1942), and a mechanism involving dehydrogenation and transient formation ofa mobile centre ofunsaturation is probably involved.…”

Section: Results and Discussion Enzymic Hydrolysis And Analysis Ofsubmentioning

confidence: 79%

Preparation and characterization of substrates suitable for the study of stereospecific secondary alkylsulphohydrolases of detergent-degrading micro-organisms

Matcham¹,

Dodgson²

1977

Biochemical Journal

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During the course of the purification of novel stereospecific secondary aklylsulphohydrolases present in certain detergent-degrading micro-organisms, it became apparent that substrates prepared by sulphating secondary alcohols with H2SO4 are heterogeneous. Apart from the racemization that occurs if resolved alcohols are sulphated, evidence is provided to show that other isomers are produced in which the position of the ester sulphate group on the alkyl chain has been altered. These changes can be avoided if pyridine/SO3 reagent (prepared with SO3) is substituted as sulphating agent. Experiments in which secondary alkyl sulphates prepared by both methods were tested as potential substrates for the two secondary alkylsulphohydrolase enzymes of Comamonas terrigena have provided initial information about the specificity of the enzymes.

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“…The answer is that they do. Hydrogen fluoride (78), phosphoric acid, and sulfuric acid (14,32) have been established as catalysts for Friedel-Crafts and similar reactions. H-acid or both may be responsible for the catalysis.…”

Section: Acid Catalysismentioning

confidence: 99%