000081641 001__ 81641
000081641 005__ 20180127194644.0
000081641 037__ $$aARTICLE
000081641 245__ $$aSite selective hydrogen/metal exchange: competition and cooperation between superbases and neighboring groups
000081641 260__ $$c1994
000081641 269__ $$a1994
000081641 336__ $$aJournal Articles
000081641 500__ $$aCAN 121:82077 21-0 General Organic Chemistry Institut Chimie Organique,Universite Lausanne,Lausanne,Switz. Journal; General Review 0033-4545 written in English. 12408-02-5 Role: RCT (Reactant), RACT (Reactant or reagent) (protonation and Proton transfer reaction, deprotonation, site selective hydrogen/metal exchange, in org. synthesis)
000081641 520__ $$aA review with 62 refs. The appropriate choice of a metalating reagent is the key to the optional deprotonation of benzylamine derivs. at a position adjacent to the substituent or the nitrogen bearing side chain or even at the benzylic a-position of the latter. Subsequent reaction with suitable electrophiles followed by cyclization affords heterocyclic products such as isoquinolines and isoindolones. Immediately when generated, some organometallic intermediates can undergo a rapid second hydrogen/metal exchange process. However, demetalation is only kinetically, not thermodn. favored as a careful investigation of typical cases has revealed. Moreover, it can be avoided if the donor capacity of the solvent or the polarity of the metalating reagent is increased. Allylic organopotassium compds. exhibit intriguing stereopreferences. This peculiarity has been exploited in a no. of very simple sesquiterpene syntheses. [on SciFinder (R)]
000081641 6531_ $$aProtonation and Proton transfer reaction (deprotonation
000081641 6531_ $$asite selective hydrogen/metal exchange
000081641 6531_ $$ain org. synthesis); Synthesis (org.
000081641 6531_ $$asite selective hydrogen/metal exchange and)
000081641 6531_ $$areview deprotonation org synthesis
000081641 700__ $$0240930$$aSchlosser, Manfred$$g123541
000081641 700__ $$aFaigl, Ferenc
000081641 700__ $$aFranzini, Livia
000081641 700__ $$aGeneste, Herve
000081641 700__ $$aKatsoulos, Georges
000081641 700__ $$aZhong, Guo Fu
000081641 773__ $$j66$$k7$$q1439-46$$tPure and Applied Chemistry
000081641 909C0 $$0252181$$pLSCO
000081641 909CO $$ooai:infoscience.tind.io:81641$$particle
000081641 937__ $$aLSCO-ARTICLE-1994-007
000081641 970__ $$a138/LSCO
000081641 973__ $$aEPFL$$rREVIEWED$$sPUBLISHED
000081641 980__ $$aARTICLE