The appropriate choice of a metalating reagent is the key to the optional deprotonation of benzylamine derivatives at a position adjacent to the substituent or the nitrogen bearing side chain or even at the benzylic a-position of the latter. Subsequent reaction with suitable electrophiles followed by cyclization affords heterocyclic products such as isoquinolines and isoindolones. - Immediately when generated, some organometallic intermediates can undergo a rapid second hydrogen/metal exchange process. However, dimetalation is only kinetically, not thermodynamically favored as a careful investigation of typical cases has revealed. Moreover, it can be avoided if the donor capacity of the solvent or the polarity of the metalating reagent is increased. - Allylic organopotassium compounds exhibit intriguing stereopreferences. This pecularity has been exploited in a number of very simple sesquiterpene syntheses.
ASJC Scopus subject areas
- Chemical Engineering(all)