000081516 001__ 81516
000081516 005__ 20180127194624.0
000081516 037__ $$aARTICLE
000081516 245__ $$aSelective syntheses with organometallics. VI. Capricious stereoselectivities of alkenylpotassium formation under kinetic and thermodynamic control. Oxygen-triggered configurational equilibration of an allyl type organometallic compound
000081516 260__ $$c1977
000081516 269__ $$a1977
000081516 336__ $$aJournal Articles
000081516 500__ $$aCAN 87:133729
000081516 500__ $$a22-9
000081516 500__ $$aPhysical Organic Chemistry
000081516 500__ $$aInst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.
000081516 500__ $$aJournal
000081516 500__ $$a0018-019X
000081516 500__ $$awritten in English.
000081516 500__ $$a690-08-4; 4050-45-7 Role: RCT (Reactant), RACT (Reactant or reagent) (metalation of, followed by reaction with oxirane); 64172-07-2P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. and conversion to tert-butylpentenal); 64172-10-7P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and reaction with pivalaldehyde); 64172-08-3P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. and redn. of aldehyde group to alc. group in); 64081-43-2P; 64081-44-3P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. and vinylation of hydroxy group in); 31502-21-3P; 54393-36-1P; 64172-09-4P; 64172-11-8P; 64172-12-9P; 64172-13-0P; 64172-14-1P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of); 630-19-3 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with (hydroxybutyl)triphenylphosphonium chloride); 603-35-0 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with 4-chloro-1-butanol); 762-63-0 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with butyllithium); 109-72-8 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with dimethylpentene); 75-21-8 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with metalated propene derivs.); 110-87-2 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with tert-butyllithium); 928-51-8 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with triphenylphosphine)
000081516 520__ $$aMetalation at the allylic site (Me group) of (Z)-RCH:CHMe (R = alkyl) is more rapid than with the E-isomers regardless of the configuration in which the resultant organometallic is more thermodn. stable. Thus, (Z)-Me3CCH:CHCH2K is formed 15 times faster than its E-isomer, although the latter is thermodn. favored. Isomerization of the allylpotassium compds. in THF is very slow, but may be catalyzed by trace impurities, e.g., O. [on SciFinder (R)]
000081516 6531_ $$aMetalation (of allylic alkenes); Isomerization (of metalated allylic alkenes); Alkenes Role: RCT (Reactant)
000081516 6531_ $$aRACT (Reactant or reagent) (allyl
000081516 6531_ $$ametalation of)
000081516 6531_ $$ametalation propene deriv kinetics; allylpotassium isomerization
000081516 700__ $$aStaehle, Manfred
000081516 700__ $$aHartmann, Juergen
000081516 700__ $$0240930$$aSchlosser, Manfred$$g123541
000081516 773__ $$j60$$k5$$q1730-8$$tHelvetica Chimica Acta
000081516 909C0 $$0252181$$pLSCO
000081516 909CO $$ooai:infoscience.tind.io:81516$$particle
000081516 937__ $$aLSCO-ARTICLE-1977-005
000081516 970__ $$a61/LSCO
000081516 973__ $$aEPFL$$rREVIEWED$$sPUBLISHED
000081516 980__ $$aARTICLE