Abstract
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)]
Details
Title
O-Fluoromethyl carboxylates and O-fluoromethyl carbamates
Author(s)
Schlosser, Manfred ; Limat, Dominique
Published in
Tetrahedron
Volume
51
Issue
20
Pages
5807-12
Date
1995
ISSN
0040-4020
Keywords
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)
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
Peer-reviewed publications
Work produced at EPFL
Journal Articles
Published
Record creation date
2006-03-03