Eileen E. Betts

At Bristol

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David B. MacLean

Velindre NHS Trust

L. R. C. Barclay

Mount Allison University

David W. Brown

Fundação Oswaldo Cruz

N. Sainsbury

At Bristol

Leonard O. Ross

SRI International

Christopher H. Barclay

University of Glasgow

S.F. Dyke

Queensland University of Technology

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At Bristol

Fundação Oswaldo Cruz

The University of Texas Southwestern Medical Center

UK Health Security Agency

Westmead Hospital

University of Missouri

Public Health England

Global Virus Network

University of the West Indies

University College London

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THE TERTIARYBUTYLBENZENES: III. THE SYNTHESIS OF 2,4,6-TRI-t-BUTYLBENZOIC ACID AND THE DISSOCIATION OF DI- AND TRI-t-BUTYLBENZOIC ACIDS

Canadian Journal of Chemistry (1955)

Eileen E. Betts L. R. C. Barclay

2,4,6-Tri-t-butylbromobenzene, m.p. 177–177.5°, was prepared by the bromination of 1,3,5-tri-t-butylbenzene in the presence of silver nitrate. The reaction of 2,4,6-tri-t-butylbromobenzene and n-butyllithium gave 2,4,6-tri-t-butylphenyl-lithium, which on carbonation yielded 2,4,6-tri-t-butylbenzoic acid, m.p. 297°. A solution of this acid in fuming sulphuric acid yielded a methyl ester, m.p. 96–98°, when it was poured into absolute methanol. Similar treatment of 1,4-di-t-butylbenzene with bromine gave 2,5-di-t-butylbromobenzene, which on reaction with n-butyllithium and subsequent carbonation gave 2,5-di-t-butylbenzoic acid. The reaction of 1,3,5-tri-t-butylbenzene with acetyl chloride in the presence of aluminum chloride gave a liquid ketone, and hypohalide oxidation of this ketone yielded 3,5-tri-t-butylbenzoic acid. The ultraviolet absorption spectra of the two bromo compounds and the three acids were measured and are discussed. The considerable acid-weakening effect in 2,4,6-tri-t-butylbenzoic acid is attributed to steric hindrance to the formation of the carboxylate anion.

Butyllithium

10.1139/v55-219

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Citations (31)

The condensation of isoquinolinium salts with aromatic aldehydes

Tetrahedron Letters (1966)

Eileen E. Betts David W. Brown S.F. Dyke N. Sainsbury

10.1016/s0040-4039(01)99960-5

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Citations (6)

LYCOPODIUM ALKALOIDS: VI. REACTIONS OF THE DIPHENYL DERIVATIVE OF DESOXODIHYDROANNOTININE

Canadian Journal of Chemistry (1958)

Eileen E. Betts David B. MacLean

Desoxodihydroannotinine reacted with phenyl lithium to yield a diphenyl derivative, C 28 H 35 O 2 N (III). This compound yielded a ketone, C 28 H 33 O 2 N (V), upon oxidation by the Oppenauer procedure and a dihydroxyketone, C 28 H 33 O 3 N (VI), upon oxidation with chromic acid. A ketone VIII, epimeric with V, was obtained by treatment of III with potassium tertiary butoxide in cyclohexanone. Both V and VIII underwent elimination of their diphenyl carbinol groups upon treatment with potassium tertiary butoxide to yield an unsaturated ketone, C 15 H 21 ON (IX), and benzohydrol. These reactions are discussed in relation to the recently proposed structures for the parent alkaloid, annotinine.

Chromic acid

Derivative (finance)

10.1139/v58-067

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Citations (3)

The t-Butylbenzenes. II. A High Melting Hydrocarbon from Friedel-Crafts Alkylation of 1,3,5-tri-t-butylbenzene with t-Butyl Chloride¹

Journal of the American Chemical Society (1955)

Leonard O. Ross Christopher H. Barclay Eileen E. Betts

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTThe t-Butylbenzenes. II. A High Melting Hydrocarbon from Friedel-Crafts Alkylation of 1,3,5-tri-t-butylbenzene with t-Butyl Chloride1L. Ross, C. Barclay, and Eileen E. BettsCite this: J. Am. Chem. Soc. 1955, 77, 21, 5735–5737Publication Date (Print):November 1, 1955Publication History Published online1 May 2002Published inissue 1 November 1955https://pubs.acs.org/doi/10.1021/ja01626a080https://doi.org/10.1021/ja01626a080research-articleACS PublicationsRequest reuse permissionsArticle Views117Altmetric-Citations9LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose Get e-Alerts

Friedel–Crafts reaction

10.1021/ja01626a080

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Citations (9)

THE TERTIARYBUTYLBENZENES: I. ALKYLATION OF 1,4-DI-t-BUTYLBENZENE WITH t-BUTYL CHLORIDE

Canadian Journal of Chemistry (1955)

L. R. C. Barclay Eileen E. Betts

The alkylation of P-di-t-butylbenzene with excess t-butyl chloride in the presence of aluminum chloride in the cold produces a new aromatic hydrocarbon, m.p. 218.5–219°. Evidence is given for the presence of an alicyclic nucleus in this hydrocarbon which analyzes for C 22 H 34 . The preparation of nitro and amino derivatives from this hydrocarbon is described. The alkylation of benzene under similar conditions yielded some 1,3,5-tri-t-butylbenzene, and an improved method of preparation of this hydrocarbon from P-di-t-butylbenzene is given.

Alicyclic compound

Aromatic hydrocarbon

10.1139/v55-079

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Citations (10)

LYCOPODIUM ALKALOIDS: V. OXIDATION AND REDUCTION STUDIES ON ANNOTININE AND ITS DERIVATIVES

Canadian Journal of Chemistry (1957)

Eileen E. Betts David B. MacLean

Annotinine lactam C 16 H 19 O 4 N has been converted by the action of dilute sulphuric acid to the lactamdiol, C 16 H 21 O 5 N. Oxidation studies on the lactamdiol have confirmed the presence of the epoxide ring in the alkaloid and have established the six-membered character of the lactam ring. The allylamine structure of unsaturated lactone A, C 16 H 21 O 2 N, has been confirmed and a number of intermediate oxidation products of this compound have been isolated and characterized. Raney nickel reduction of annotinine yielded hydroxy annotinine, C 16 H 23 O 3 N, and saturated lactone A, C 16 H 23 O 2 N. Catalytic reduction of annotinine lactam over Adams′ catalyst in acidic medium converted it partially to annotinine.

Lactam

Raney nickel

Allylamine

Catalytic hydrogenation

Birch reduction

10.1139/v57-032

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Citations (7)