Résumé
The fluoride catalyzed reaction between acyl fluorides and monomeric formaldehyde affords fluoromethyl carboxylates in acceptable yields. Fluoromethyl fluoroformate, readily accessible from the corresponding dichloro compd., condenses with amines to give fluoromethyl carbamates. [on SciFinder (R)]
Détails
Titre
O-Fluoromethyl carboxylates and O-fluoromethyl carbamates
Auteur(s)
Schlosser, Manfred ; Limat, Dominique
Publié dans
Tetrahedron
Volume
51
Numéro
20
Pages
5807-12
Date
1995
ISSN
0040-4020
Mots-clés (libres)
Acetalization and Ketalization; Addition reaction; Addition reaction catalysts (O-fluoromethyl carboxylates and O-fluoromethyl carbamates); Acid fluorides; Amines Role: RCT (Reactant); RACT (Reactant or reagent) (O-fluoromethyl carboxylates and O-fluoro; carboxylate fluoromethyl; carbamate fluoromethyl
Note
CAN 123:142990
21-2
General Organic Chemistry
Inst. CHim. Org.,Univ. Batiment Chim.,Lausanne-Dorigny,Switz.
Journal
written in English.
5342-31-4P (Methylene dibenzoate); 20177-68-8P; 32720-34-6DP; 166331-88-0P; 166331-89-1P Role: BYP (Byproduct), PREP (Preparation) (O-fluoromethyl carboxylates and O-fluoromethyl carbamates); 17455-13-9 (18-Crown-6); 59201-86-4 (Tris(diethylamino)sulfonium difluorotrimethylsilicate) Role: CAT (Catalyst use), USES (Uses) (O-fluoromethyl carboxylates and O-fluoromethyl carbamates); 7789-23-3 (Potassium fluoride) Role: CAT (Catalyst use), RCT (Reactant), USES (Uses), RACT (Reactant or reagent) (O-fluoromethyl carboxylates and O-fluoromethyl carbamates); 100-46-9 (Benzylamine); 104-94-9 (p-Anisidine); 109-73-9 (Butylamine); 136-95-8 (2-Aminobenzothiazole); 288-32-4 (Imidazole); 334-19-0 (Heptanoyl fluoride); 455-32-3 (Benzoyl fluoride); 693-34-5 (Adipoyl fluoride); 1977-87-3 (Cyclohexanecarbonyl fluoride); 22128-62-7 (Chloromethyl chloroformate); 31174-04-6 (2-Furoyl fluoride) Role: RCT (Reactant), RACT (Reactant or reagent) (O-fluoromethyl carboxylates and O-fluoromethyl carbamates); 2838-04-2P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (O-fluoromethyl carboxylates and O-fluoromethyl carbamates); 166331-78-8P; 166331-79-9P; 166331-80-2P; 166331-81-3P; 166331-82-4P; 166331-83-5P; 166331-84-6P; 166331-85-7P; 166331-86-8P; 166331-87-9P Role: SPN (Synthetic preparation), PREP (Preparation) (O-fluoromethyl carboxylates and O-fluoromethyl carbamates); 50-00-0 (Formaldehyde) Role: RCT (Reactant), RACT (Reactant or reagent) (monomeric; O-fluoromethyl carboxylates and O-fluoromethyl carbamates)
21-2
General Organic Chemistry
Inst. CHim. Org.,Univ. Batiment Chim.,Lausanne-Dorigny,Switz.
Journal
written in English.
5342-31-4P (Methylene dibenzoate); 20177-68-8P; 32720-34-6DP; 166331-88-0P; 166331-89-1P Role: BYP (Byproduct), PREP (Preparation) (O-fluoromethyl carboxylates and O-fluoromethyl carbamates); 17455-13-9 (18-Crown-6); 59201-86-4 (Tris(diethylamino)sulfonium difluorotrimethylsilicate) Role: CAT (Catalyst use), USES (Uses) (O-fluoromethyl carboxylates and O-fluoromethyl carbamates); 7789-23-3 (Potassium fluoride) Role: CAT (Catalyst use), RCT (Reactant), USES (Uses), RACT (Reactant or reagent) (O-fluoromethyl carboxylates and O-fluoromethyl carbamates); 100-46-9 (Benzylamine); 104-94-9 (p-Anisidine); 109-73-9 (Butylamine); 136-95-8 (2-Aminobenzothiazole); 288-32-4 (Imidazole); 334-19-0 (Heptanoyl fluoride); 455-32-3 (Benzoyl fluoride); 693-34-5 (Adipoyl fluoride); 1977-87-3 (Cyclohexanecarbonyl fluoride); 22128-62-7 (Chloromethyl chloroformate); 31174-04-6 (2-Furoyl fluoride) Role: RCT (Reactant), RACT (Reactant or reagent) (O-fluoromethyl carboxylates and O-fluoromethyl carbamates); 2838-04-2P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (O-fluoromethyl carboxylates and O-fluoromethyl carbamates); 166331-78-8P; 166331-79-9P; 166331-80-2P; 166331-81-3P; 166331-82-4P; 166331-83-5P; 166331-84-6P; 166331-85-7P; 166331-86-8P; 166331-87-9P Role: SPN (Synthetic preparation), PREP (Preparation) (O-fluoromethyl carboxylates and O-fluoromethyl carbamates); 50-00-0 (Formaldehyde) Role: RCT (Reactant), RACT (Reactant or reagent) (monomeric; O-fluoromethyl carboxylates and O-fluoromethyl carbamates)
Laboratoires
LSCO
Le document apparaît dans
Production scientifique et compétences > SB - Faculté des sciences de base > SB Archives > LSCO - Laboratoire de synthèse organique et catalyse
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Articles de journaux
Publié
Publications validées par des pairs
Travail produit à l'EPFL
Articles de journaux
Publié
Date de création de la notice
2006-03-03