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By Ramsay W., Donnan F.G.

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Generalites sur les reactions 31 Dipolarophiles A) Derives d'alcenes et de composes « azo » : CH2=CH-CN, CH2=CH-COOR (R = alkyl), CH2=C(Me)-COOR, CH2=CH-CO-R (R = alkyl ou aryl), Ph-CH=CH-NO2, EtCO2-CH=CH-CO2Et (Zet £), NC-CH=CH-CN (£), CH2=CH-Ph, Ph-CH=CH-Ph, anhydride maleique, maleimide, EtOgC-ISkN-CC^Et B) Derives d'alcynes : R-O=C-R' (R et R1 = aryl ou heteroaryl), R-CsCH (R = aryl ou heteroaryl), RO2C-CsC-CO2R (R = Me ou Et), NC-C^C-CN, R-CO-OC-CO-R' (R = Me, Et, R' = aryl ou heteroaryl) HC=C-CO2R (R = Me ou Et) C) Benzyne D) Heterocumulenes : R-N=C=O, R-N-C=S (R = alkyl ou aryl), R-CO-N=C=O, R-CO-N=C=S (aryl ou CCy E) Fonctions simples : R-C^N, R-C(R)=N-R' (R et R' = alkyl ou aryl).

Ce sont des composes tres reactifs avec les acides, les bases et les reactifs nucleophiles comme les amines, les alcools... C'est ce qui explique leur tres forte toxicite et leur pouvoir cancerogene. Ce sont done des produits a manipuler avec beaucoup de precautions. 1 Oxiranes Les reactions des oxiranes sont nombreuses et leurs resultats dependent du milieu (solvant, pH), des substituants et de la stereochimie de la molecule. L'ouverture du cycle se fait souvent de maniere stereoselective et regioselective d'ou son interet dans les syntheses totales des molecules d'origine naturelle.

Elles reagissent avec I'acrylate d'ethyle et I'acrylonitrile selon la reaction d'addition de Michael. Les cetenes s'additionnent pour donner des derives acyles. L'acylation par les chlorures d'acides est effectuee en presence de triethylamine, afin d'eviter la formation de sels d'aziridinium, susceptibles de favoriser I'ouverture du cycle. L'action de I'hypochlorite de sodium conduit a des chloramines, les N-chloro aziridines. 3. 3 Reactions d'ouverture du cycle L'ouverture du cycle est favorisee par la presence de substituants electroattracteurs sur les carbones cycliques et par un milieu reactionnel faiblement acide.

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A system of physical chemistry by Ramsay W., Donnan F.G.


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