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Synthesis and photochemistry of α-substituted carbonyl compounds / Ahmed M'hamedi 

Public ISBD Titre : Synthesis and photochemistry of α-substituted carbonyl compounds Type de document : texte imprimé Auteurs : Ahmed M'hamedi, Auteur ; J. Hill, Directeur de thèse Editeur : University of Salford Année de publication : 1992 Importance : 138 f. Format : 30 cm. Note générale : Thèse de Doctorat : Génie Chimique : Salford, University of Salford : 1992 Bibliogr. f. 139 - 153 Langues : Anglais (eng) Mots-clés : α-substituted  carbonyl  compounds Photochemistry α-amino-enones Coumarins Irradiation α-N-Methylaniliosuccinimides Cyclisation Index. décimale : D001292 Résumé : The work described in this thesis deals with various aspects of the photochemistry of α-substituted carbonyl compounds, and is made up of three parts. 1. α-amino-enones: As part of studies into the photochemistry of α-amino-carbonyl compounds, α-amino-enones 1a and 1b and coumarins 4a and 4b were synthesised and irradiated. Irradiation of 1a yielded the azetidinol 3a and enone isomers 2a, and 1b gave impure azetidinol 3b and enone isomers 2b. On the other hand, coumarin 4a and 4b gave complex photoproduct mixtures. 2. α-N-methylanilinosuccinimides and related compounds 2-(N-mthylanilino)-N-substituted succinimides 5a-c were synthesised and irradiated. These compounds were prepared from maleic anhydride via the corresponding N-substituted maleimides. Irradiation of 5a-c gave the pararearrangement products 6a-c respectively, generally as the major photoproduct. The ortho-rearrangement product 7 was also obtained from 5a. No significant photoproducts were formed from N-benzylsuccinimide 8. 2-(N-Methylanilino)-N-phenylmaleimide 9, prepared from N-phenylmaleimide, was irradiated, but no product could be isolated from the complex photolysis mixture. The succinimide 11, prepared from itaconic anhydride 10, gave a fused-ring photoproduct 12 as a result of a type II cyclisation. 3. Unsaturated α-substituted carbonyl compounds: Radical cyclisations. A variety of α-substituted compounds were irradiated in a study into the use of such photoreactions as a method for radical cyclisations. a/ Unsaturated β-ketosulphides 13 and 14 were prepared. Irradiation gave the cyclisation product 17 and 18 respectively. Unsaturated β-ketoester-sulphides 15 and 16a-e were synthesised. Irradiation of 15 and 16d yielded the cyclisation products 19 and 20 respectively. However, irradiation of 16 a and 16 d gave complex mixtures from which no product could be isolated. b/ α-Substituted esters 22a-c were synthesised via chloroester 21. Irradiation of 22a and 22b yielded the non-cyclised products 23 and 24 respectively. No significant product aws produced on irradiation of 22c. c/ Aseries of α-substituted amides 25a-f were synthesised. Irradiation of 25a and 25d yielded the cyclisation products 26 and 27 respectively, whereas 25a gave diallylacetamide 28 on irradiation in the presence of benzyl mercaptan. Amides 25b, c, e and f gave the corresponding non-cyclised acetamides 29 a or b. Synthesis and photochemistry of α-substituted carbonyl compounds [texte imprimé] / Ahmed M'hamedi, Auteur ; J. Hill, Directeur de thèse . - [S.l.] : University of Salford, 1992 . - 138 f. ; 30 cm. Thèse de Doctorat : Génie Chimique : Salford, University of Salford : 1992 Bibliogr. f. 139 - 153 Langues : Anglais (eng) Mots-clés : α-substituted  carbonyl  compounds Photochemistry α-amino-enones Coumarins Irradiation α-N-Methylaniliosuccinimides Cyclisation Index. décimale : D001292 Résumé : The work described in this thesis deals with various aspects of the photochemistry of α-substituted carbonyl compounds, and is made up of three parts. 1. α-amino-enones: As part of studies into the photochemistry of α-amino-carbonyl compounds, α-amino-enones 1a and 1b and coumarins 4a and 4b were synthesised and irradiated. Irradiation of 1a yielded the azetidinol 3a and enone isomers 2a, and 1b gave impure azetidinol 3b and enone isomers 2b. On the other hand, coumarin 4a and 4b gave complex photoproduct mixtures. 2. α-N-methylanilinosuccinimides and related compounds 2-(N-mthylanilino)-N-substituted succinimides 5a-c were synthesised and irradiated. These compounds were prepared from maleic anhydride via the corresponding N-substituted maleimides. Irradiation of 5a-c gave the pararearrangement products 6a-c respectively, generally as the major photoproduct. The ortho-rearrangement product 7 was also obtained from 5a. No significant photoproducts were formed from N-benzylsuccinimide 8. 2-(N-Methylanilino)-N-phenylmaleimide 9, prepared from N-phenylmaleimide, was irradiated, but no product could be isolated from the complex photolysis mixture. The succinimide 11, prepared from itaconic anhydride 10, gave a fused-ring photoproduct 12 as a result of a type II cyclisation. 3. Unsaturated α-substituted carbonyl compounds: Radical cyclisations. A variety of α-substituted compounds were irradiated in a study into the use of such photoreactions as a method for radical cyclisations. a/ Unsaturated β-ketosulphides 13 and 14 were prepared. Irradiation gave the cyclisation product 17 and 18 respectively. Unsaturated β-ketoester-sulphides 15 and 16a-e were synthesised. Irradiation of 15 and 16d yielded the cyclisation products 19 and 20 respectively. However, irradiation of 16 a and 16 d gave complex mixtures from which no product could be isolated. b/ α-Substituted esters 22a-c were synthesised via chloroester 21. Irradiation of 22a and 22b yielded the non-cyclised products 23 and 24 respectively. No significant product aws produced on irradiation of 22c. c/ Aseries of α-substituted amides 25a-f were synthesised. Irradiation of 25a and 25d yielded the cyclisation products 26 and 27 respectively, whereas 25a gave diallylacetamide 28 on irradiation in the presence of benzyl mercaptan. Amides 25b, c, e and f gave the corresponding non-cyclised acetamides 29 a or b.

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