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"La r  action d Ing-Manske est une variante tr  s utilis  e de la r  action de Gabriel qui permet notamment la synth  se d amines primaires dans des conditions relativement douces  Cependant  son m  canisme n a jamais fait l objet d   tudes th  oriques approfondies et seuls quelques interm  diaires ont pu   tre isol  s ou mis en   vidence lors de travaux exp  rimentaux  Par ailleurs  son utilisation avec le pyraz  pate de m  thyle a pr  sent   un caract  re diast  r  os  lectif in  dit que nous avons cherch        lucider  Le m  canisme intime de la r  action a   t     tudi   au niveau DFT-B3LYP  Les   tats de transition et les   tats interm  diaires pour diff  rentes voies r  actionnelles ont   t   d  termin  s  Les effets de solvants ont   t   pris en compte via les effets de la microsolvation coupl  s ou non aux effets    longue distance  Enfin l application du m  canisme pr  f  rentiel au pyraz  pate de m  thyle a permis de proposer une rationalisation de la diast  r  os  lectivit   observ  e    The Ing-Manske reaction is a well-known variant of the Gabriel synthesis reaction which is used to synthetize primary amines under mild conditions  Yet  its mechanism has never been theoretically studied  Only few intermediates have been experimentally isolated or characterised  Its use with methyl pyrazepate showed an unexpected diastereoselective behavior that we have tried to clarify  The mechanism has been studied at the DFT-B3LYP level  Transition states and reaction intermediates have been calculated for various possible reaction pathways  Solvation effects  either microsolvatation or bulk effects  via PCM method   have been taken into account  On this basis some rationalization for the observed diastereoselectivity is proposed    STRASBOURG-Sc  et Techniques  674822102    Sudoc   Sudoc   France   FR"
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