A novel and versatile access to fluorinated carbo- and heterocyclic compounds employing electron-rich fluorodienes as cycloaddition components
Shi, Guo-qiang; Schlosser, Manfred
1993

Abstract

The readily accessible 2-fluoro-1-trimethylsiloxy-1,3-dienes undergo Diels-Alder type cycloaddn. with a variety of dienophiles under mild conditions. In this way, fluoro-2-cyclohexenols, fluoro-2,5-dihydropyranols, fluoro-2,5-dihydro-2-pyridinols, fluoropyridines, fluoro-3,6-dihydro-1,2-oxazines and fluoropyrroles can be efficiently prepd. [on SciFinder (R)]

Details

Title A novel and versatile access to fluorinated carbo- and heterocyclic compounds employing electron-rich fluorodienes as cycloaddition components
Author(s) Shi, Guo-qiang ; Schlosser, Manfred
Published in Tetrahedron
Volume 49
Issue 7
Pages 1445-56
Date 1993
ISSN 0040-4020
Keywords
Note CAN 119:48721
21-2
General Organic Chemistry
Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.
Journal
written in English.
96-33-3; 106-51-4 (p-Benzoquinone); 108-31-6 (2,5-Furandione); 481-39-0 (Juglone); 586-96-9 (Nitrosobenzene); 609-09-6 (Diethyl mesoxalate); 623-47-2 (Ethyl propiolate); 762-42-5 (Dimethyl acetylenedicarboxylate); 873-92-7 (1-Chloro-1-nitrocyclohexane); 13707-44-3; 17640-15-2 (Methyl cyanoformate); 60656-87-3; 83670-53-5 Role: RCT (Reactant), RACT (Reactant or reagent) (cycloaddn. reaction of, with butadiene deriv.); 146271-54-7; 148541-85-9 Role: RCT (Reactant), RACT (Reactant or reagent) (cycloaddn. reactions of); 63995-82-4 (2-Fluoro-3-methyl-2-butenal) Role: RCT (Reactant), RACT (Reactant or reagent) (dimerization of); 148541-52-0P; 148541-53-1P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and cycloaddn. reactions of); 148541-78-0P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. and elimination of); 148541-87-1P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and elimination reaction of); 148541-67-7P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and hydride redn. of); 148541-73-5P; 148541-74-6P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and hydrolysis of); 148541-66-6P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and methoxylation of); 148541-60-0P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and oxidn. of); 148541-82-6P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and silylation of); 86239-00-1P; 148541-54-2P; 148541-55-3P; 148541-56-4P; 148541-57-5P; 148541-58-6P; 148541-59-7P; 148541-61-1P; 148541-62-2P; 148541-63-3P; 148541-64-4P; 148541-65-5P; 148541-68-8P; 148541-69-9P; 148541-70-2P; 148541-71-3P; 148541-72-4P; 148541-75-7P; 148541-76-8P; 148541-77-9P; 148541-79-1P; 148541-80-4P; 148541-81-5P; 148541-86-0P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of); 148541-83-7; 148541-84-8 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with dichlorofluoromethane); 75-43-4 (Dichlorofluoromethane) Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with methoxy(trimethylsilyloxy)propene); 82147-66-8 Role: RCT (Reactant), RACT (Reactant or reagent) (silylation of)
DOI https://doi.org/10.1016/S0040-4020(01)90196-6
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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