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  4. 1-(Triphenylmethyl)allylpotassium: conformational preference and [1,2]-rearrangement
 
research article

1-(Triphenylmethyl)allylpotassium: conformational preference and [1,2]-rearrangement

Moret, Etienne
•
Fuerrer, Juerg
•
Schlosser, Manfred  
1988
Tetrahedron

Upon treatment with the superbasic 1:1 mixt. of BuLi and Me3COK, cis- and trans-1,1,1-triphenyl-2-butene as well as 4,4,4-triphenyl-1-butene undergo a hydrogen/metal exchange to afford 1-(triphenylmethyl)allylpotassium [4,4,4-triphenyl-2-butenylpotassium] which exists in two stereoisomeric forms. Torsional equilibration leads to an endo/exo ratio of approx. 50:50. Novel endo-stabilizing interactions are discussed to rationalize this result. At temps. around or above 0 Deg, a Ph 1,2-migration, though no 1,4-migration, takes place. [on SciFinder (R)]

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Type
research article
DOI
10.1016/S0040-4020(01)85984-6
Author(s)
Moret, Etienne
Fuerrer, Juerg
Schlosser, Manfred  
Date Issued

1988

Published in
Tetrahedron
Volume

44

Issue

12

Start page

3539

End page

50

Subjects

Rearrangement (of triphenylmethylallylpotassium)

•

phenylmethylallylpotassium formation conformational preference rearrangement; rearrangement conformation triphenylmethylallylpotassium

Note

CAN 111:7452

29-2

Organometallic and Organometalloidal Compounds

Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.

Journal

written in English.

1530-32-1 (Ethyltriphenylphosphonium bromide) Role: RCT (Reactant), RACT (Reactant or reagent) (Wittig reaction by, of triphenylacetaldehyde); 106-95-6 (Allylbromide) Role: RCT (Reactant), RACT (Reactant or reagent) (allylation by, of triphenylmethane, triphenylbutene by); 519-73-3 (Triphenylmethane) Role: RCT (Reactant), RACT (Reactant or reagent) (allylation of, with allyl bromide, triphenylbutene by); 119297-15-3P; 119297-16-4P Role: RCT (Reactant), PREP (Preparation), RACT (Reactant or reagent) (formation and rearrangement of); 42365-04-8P (Triphenylacetaldehyde) Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and Wittig reaction of, with ethylenetriphenylphosphorane); 16876-20-3P (4,4,4-Triphenyl-1-butene) Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and catalyzed isomerization of); 121136-58-1P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and hydrolysis of); 121136-50-3P; 121136-51-4P; 121136-54-7P; 121136-55-8P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and methylation of); 121136-48-9P; 121136-49-0P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and methylation of, conformation preference in relation to); 121136-52-5P; 121136-53-6P; 121136-56-9P; 121136-57-0P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of)

Editorial or Peer reviewed

REVIEWED

Written at

EPFL

EPFL units
LSCO  
Available on Infoscience
March 3, 2006
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/226844
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