Base Promoted 1,4-Elimination Reactions : On the Origin of an Eventual syn-Stereoselectivity
Schlosser, Manfred; Tarchini, Claudio; Tran Dinh, An; Ruzziconi, Renzo; Bauer, Paul J.
1981

Abstract

Rate ratios were obtained for the base-catalyzed 1,4-dehydrochlorination of (E)- and (Z)-Me3CCCl:C:C:CClCMe3 to give Me3CC.tplbond.CC.tplbond.CCMe3. In the KOMe/MeOH or KOCMe3/Me2SO systems the reactivity of both isomers was similar. With KOCMe3 in Me3COH, THF or C6H6 the 2 isomers exhibited similar reactivity when 18-crown-6 was present, but the E isomer was much more reactive in its absence. These findings suggested a conveyor-belt-type transition state with an aggregate of the base interacting with the H and Cl atoms undergoing elimination. [on SciFinder (R)]

Details

Title Base Promoted 1,4-Elimination Reactions : On the Origin of an Eventual syn-Stereoselectivity
Author(s) Schlosser, Manfred ; Tarchini, Claudio ; Tran Dinh, An ; Ruzziconi, Renzo ; Bauer, Paul J.
Published in Angewandte Chemie, International Edition
Volume 20
Pages 1041-1042
Date 1981
Keywords
Note CAN 96:51540 22-4 Physical Organic Chemistry Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz. Journal 0044-8249 written in German. 79898-97-8 Role: RCT (Reactant), RACT (Reactant or reagent) (chlorination of); 79898-98-9 Role: RCT (Reactant), RACT (Reactant or reagent) (dehydrochlorination of); 79898-95-6; 79898-96-7 Role: RCT (Reactant), RACT (Reactant or reagent) (dehydrochlorination of, mechanism of); 6130-98-9P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of)
DOI https://doi.org/10.1002/anie.198110411
Laboratories LSCO
Record Appears in Scientific production and competences > SB - School of Basic Sciences > SB Archives > LSCO - Laboratory of Organic Synthesis and Catalysis
Peer-reviewed publications
Work produced at EPFL
Journal Articles
Published
Record creation date 2006-03-03

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