000081705 001__ 81705
000081705 005__ 20180127194654.0
000081705 0247_ $$2doi$$a10.1016/S0040-4039(99)02160-7
000081705 037__ $$aARTICLE
000081705 245__ $$aThe rate retarding effect of alkyl groups on arene metalation quantified
000081705 260__ $$c2000
000081705 269__ $$a2000
000081705 336__ $$aJournal Articles
000081705 500__ $$aCAN 132:237116
000081705 500__ $$a29-2
000081705 500__ $$aOrganometallic and Organometalloidal Compounds
000081705 500__ $$aSection de Chimie (BCh), Universite,Lausanne,Switz.
000081705 500__ $$aJournal
000081705 500__ $$a0040-4039
000081705 500__ $$awritten in English.
000081705 500__ $$a71-43-2 (Benzene); 98-06-6 (tert-Butylbenzene); 1012-72-2; 1014-60-4; 4834-33-7; 91324-94-6; 113710-83-1 Role: PEP (Physical, engineering or chemical process), PRP (Properties), RCT (Reactant), PROC (Process), RACT (Reactant or reagent) (rate retarding effect of alkyl groups on arene metalation quantified); 124-38-9 (Carbon dioxide) Role: RCT (Reactant), RACT (Reactant or reagent) (rate retarding effect of alkyl groups on arene metalation quantified); 14034-95-8P; 100971-92-4P; 146271-67-2P; 261788-75-4P; 261788-76-5P Role: SPN (Synthetic preparation), PREP (Preparation) (rate retarding effect of alkyl groups on arene metalation quantified); 109-72-8; 865-47-4 Role: PEP (Physical, engineering or chemical process), PRP (Properties), RCT (Reactant), PROC (Process), RACT (Reactant or reagent) (superbase; rate retarding effect of alkyl groups on arene metalation quantified)
000081705 520__ $$aMetalation/trapping sequences applied to relatively inert, tert-alkyl substituted arenes tend to give poor yields unless the reagent is used in high concns. Under optimized conditions, even 1,4-bis(tert-butyl)benzene, 1,1,3,3-tetramethylindane and 1,1,2,2,3,3-hexamethylindane can be smoothly converted into derivs. Competition expts. enable the quant. assessment of tert-alkyl substituent effects on the metalation rates at arom. ortho, meta and para positions. Unlike alkyl groups, hetero elements generally accelerate metalation reactions. 1,1,3,3-Tetramethyl-1,3-dihydroisobenzofuran undergoes the H/metal exchange 3-6 times faster than the indanes mentioned above, the reaction occurring at both the 5- and at the 4-position. [on SciFinder (R)]
000081705 6531_ $$aHeterocyclic compounds; Heterocyclic compounds Role: PEP (Physical
000081705 6531_ $$aengineering or chemical process)
000081705 6531_ $$aPRP (Properties)
000081705 6531_ $$aRCT (Reactant)
000081705 6531_ $$aPROC (Process)
000081705 6531_ $$aRACT (Reactant or reagent) (arom.; rate retarding effect of alkyl groups on arene metalation quantifi
000081705 6531_ $$aretarding effect tertiary alkyl group arene metalation kinetics LFER
000081705 700__ $$aBaston, Eckhard
000081705 700__ $$aWang, Qian
000081705 700__ $$0240930$$aSchlosser, Manfred$$g123541
000081705 773__ $$j41$$k5$$q667-670$$tTetrahedron Letters
000081705 909C0 $$0252181$$pLSCO
000081705 909CO $$ooai:infoscience.tind.io:81705$$particle
000081705 937__ $$aLSCO-ARTICLE-2000-005
000081705 970__ $$a260/LSCO
000081705 973__ $$aEPFL$$rREVIEWED$$sPUBLISHED
000081705 980__ $$aARTICLE