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Quinone methides related to 1-naphthol / Nourreddine Beghidja 

Public ISBD Titre : Quinone methides related to 1-naphthol Type de document : texte imprimé Auteurs : Nourreddine Beghidja, Auteur ; J. Carnduff, Directeur de thèse Editeur : Glasgow : University of Glasgow Année de publication : 1986 Importance : 113 f. Présentation : ill. Format : 27 cm. Note générale : Mémoire de Master : Génie Chimique : Ecosse, University of Glasgow : 1986 Bibliogr. f. 114 - 118 Langues : Anglais (eng) Mots-clés : 1-naphthol Quinone  methides Carbon  disulphide Dibromoethane Paraisomer Dihydrophenol 2-Methyl-naphthoquinonemethide Index. décimale : Ms00286 Résumé : This thesis contains three short reviews as follows: 1/ Reaction of 1-naphthol with electrophiles 2/ Formylation of 1-naphthol 3/ Preparation methods and different types of reactionsof quinone methides. Repetition of treatment of 1-naphthol with carbon disulphide and then dibromoethane gives the two isomeric quinonemethides (A) and (B) and not, as claimed earlier, exclusively the para isomer. The major product of this reaction is proved to be the ortho one by detailed analysis of its spectra and by reduction via a dihydroderivative to 2-methyl-1-naphthol which was prepared independently for comparaison. The para isomer is present in very small amount but it can be isolated by chromatography and its structure confirmed spectroscopically. This thesis describes an investigation of a specific route to the para isomer. Several methods to formylate 1-naphthol were investigated. The Gattermann Adams reaction proved most effective. The dihydrophenol (c) was made from 4-formyl-1-naphthol but attempts using a wide range of oxidising agents failed to convert it to (A). The 2-bromoderivative also failed undergo clean oxidation. 2-Methyl-naphthoquinonemethide (D) was prepared by the CS₂ reaction and characterised, but 2-chloro- and 2-bromonaphthols failed to give the corresponding quinone methide. Changing the solvent of the original reaction of 1-naphthol gave the two isomers in the ratio (1:1). The two isomers were successfully isolated and fully characterised and their spectra is reported. The nmr spectra of (A) were found to be affected by the presence of acid. Quinone methides related to 1-naphthol [texte imprimé] / Nourreddine Beghidja, Auteur ; J. Carnduff, Directeur de thèse . - Glasgow : University of Glasgow, 1986 . - 113 f. : ill. ; 27 cm. Mémoire de Master : Génie Chimique : Ecosse, University of Glasgow : 1986 Bibliogr. f. 114 - 118 Langues : Anglais (eng) Mots-clés : 1-naphthol Quinone  methides Carbon  disulphide Dibromoethane Paraisomer Dihydrophenol 2-Methyl-naphthoquinonemethide Index. décimale : Ms00286 Résumé : This thesis contains three short reviews as follows: 1/ Reaction of 1-naphthol with electrophiles 2/ Formylation of 1-naphthol 3/ Preparation methods and different types of reactionsof quinone methides. Repetition of treatment of 1-naphthol with carbon disulphide and then dibromoethane gives the two isomeric quinonemethides (A) and (B) and not, as claimed earlier, exclusively the para isomer. The major product of this reaction is proved to be the ortho one by detailed analysis of its spectra and by reduction via a dihydroderivative to 2-methyl-1-naphthol which was prepared independently for comparaison. The para isomer is present in very small amount but it can be isolated by chromatography and its structure confirmed spectroscopically. This thesis describes an investigation of a specific route to the para isomer. Several methods to formylate 1-naphthol were investigated. The Gattermann Adams reaction proved most effective. The dihydrophenol (c) was made from 4-formyl-1-naphthol but attempts using a wide range of oxidising agents failed to convert it to (A). The 2-bromoderivative also failed undergo clean oxidation. 2-Methyl-naphthoquinonemethide (D) was prepared by the CS₂ reaction and characterised, but 2-chloro- and 2-bromonaphthols failed to give the corresponding quinone methide. Changing the solvent of the original reaction of 1-naphthol gave the two isomers in the ratio (1:1). The two isomers were successfully isolated and fully characterised and their spectra is reported. The nmr spectra of (A) were found to be affected by the presence of acid.

Exemplaires

Code-barres	Cote	Support	Localisation	Section	Disponibilité	Spécialité	Etat_Exemplaire
Ms00286	Ms00286	Papier	Bibliothèque centrale	Mémoire de Master	Disponible

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