Attempted and accomplished syntheses of a few monofluorinated chrysanthemic acid derivatives
Cottens, Sylvain; Schlosser, Manfred
1988

Abstract

A sulfone mediated approach presumably did produce Me a-fluorochrysanthemate I but, if formed, the latter immediately underwent dehydrofluorination under the strongly basic reaction conditions. The cis- and trans-isomers of Me b- and g-fluorochysanthemates II and III were concomitantly obtained by treating 3-fluoro-2,5-dimethyl-2,4-hexadiene with N2CH2CO2Me in the presence of catalytic amts. of Rh(OAc)2. After enzymic and chromatog. sepn. the four individual components were converted to the m-phenoxybenzyl esters. [on SciFinder (R)]

Details

Title Attempted and accomplished syntheses of a few monofluorinated chrysanthemic acid derivatives
Author(s) Cottens, Sylvain ; Schlosser, Manfred
Published in Tetrahedron
Volume 44
Issue 23
Pages 7127-44
Date 1988
ISSN 0040-4020
Keywords
Note CAN 111:214709
30-10
Terpenes and Terpenoids
Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.
Journal
written in English.
63995-82-4 (2-Fluoro-3-methyl-2-butenal) Role: RCT (Reactant), RACT (Reactant or reagent) (carbonyl oxidn. or Wittig reactions of); 15543-64-3 Role: RCT (Reactant), RACT (Reactant or reagent) (condensation of, with fluorobutenoate); 764-13-6 (2,5-Dimethyl-2,4-hexadiene) Role: RCT (Reactant), RACT (Reactant or reagent) (cyclopropenation and competition expts. of, vs. its fluoro derivs.); 82147-66-8P (Methyl 2-fluoro-3-methyl-2-butenoate) Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. and condensation of, with butenyl tolyl sulfone); 123502-19-2P; 123502-20-5P; 123502-21-6P; 123502-22-7P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and esterification of); 123502-15-8P; 123502-16-9P; 123502-17-0P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and hydrolysis of); 76827-57-1P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and reaction of, with diazoacetate); 95887-29-9P; 123502-01-2P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and reactions of, with diazoacetates); 123502-03-4P; 123502-04-5P; 123502-06-7P; 123502-07-8P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and transesterification of); 4638-92-0DP; 123502-00-1P; 123502-02-3P; 123502-05-6P; 123502-09-0P; 123502-10-3P; 123502-18-1P; 123521-96-0P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of); 123502-08-9P; 123502-11-4P; 123502-12-5P; 123502-13-6P; 123539-92-4P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of, as potential pyrethroid); 123502-23-8P; 123502-24-9P; 123502-25-0P; 123502-26-1P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of, as potential pyrethroids); 123502-14-7P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn., ring cleavage, and hydrolysis of); 76-09-5 (Pinacol) Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with chlorofluoromethoxycyclopropane); 123501-99-5 Role: RCT (Reactant), RACT (Reactant or reagent) (ring opening reactions of); 13826-35-2 Role: RCT (Reactant), RACT (Reactant or reagent) (transesterification by, of fluorochrysanthemate Me esters)
DOI https://doi.org/10.1016/S0040-4020(01)86081-6
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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