Publication

1- and 2-fluoroalkyl carboxylates

Manfred Schlosser
1995
Journal Articles

Abstract

The 2-fluoroalkyl esters, e.g. FCH2CH2CO2Me are readily accessible by the base-catalyzed acylation of fluorohydrines. A two-step procedure is required to prep. the 1-fluoroalkyl esters: conversion of alk-1-enyl carboxylates ("ene esters") into the 2-bromo-1-fluoroalkyl esters by simultaneous treatment with N-bromosuccinimide and HF followed by the reductive replacement of bromine by tributyltin hydride. Alka-1,3-dienyl carboxylates ("diene esters") undergo 1,4-addn. of bromine and fluorine. The resulting 4-bromo-1-fluoralk-2-enyl carboxylates undergo a substitution reaction with sodium benzenesulfinate to afford the sulfones or oxidn. with DMSO to yield the 4-oxo derivs. 2-Fluoroethanol was added to NaH followed by AcOH to give 2-fluoroacetate. 2-Bromo-1-fluoroethyl acetate (prepn. given) and Bu3SnH were kept at 90 Deg for 1 h to give 1-fluoroethyl acetate. [on SciFinder (R)]

Official source

https://infoscience.epfl.ch/entities/publication/248bfc39-cee5-4cd0-bf11-a0643a9c53de

About this result

This page is automatically generated and may contain information that is not correct, complete, up-to-date, or relevant to your search query. The same applies to every other page on this website. Please make sure to verify the information with EPFL's official sources.

Graph Chat

Chat with Graph Search

Ask any question about EPFL courses, lectures, exercises, research, news, etc. or try the example questions below.

DISCLAIMER: The Graph Chatbot is not programmed to provide explicit or categorical answers to your questions. Rather, it transforms your questions into API requests that are distributed across the various IT services officially administered by EPFL. Its purpose is solely to collect and recommend relevant references to content that you can explore to help you answer your questions.

Manfred Schlosser
1995
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/248bfc39-cee5-4cd0-bf11-a0643a9c53de

About this result

Related concepts (26)

Substitution reaction

A substitution reaction (also known as single displacement reaction or single substitution reaction) is a chemical reaction during which one functional group in a chemical compound is replaced by another functional group. Substitution reactions are of prime importance in organic chemistry. Substitution reactions in organic chemistry are classified either as electrophilic or nucleophilic depending upon the reagent involved, whether a reactive intermediate involved in the reaction is a carbocation, a carbanion or a free radical, and whether the substrate is aliphatic or aromatic.

Nucleophilic substitution

In chemistry, a nucleophilic substitution is a class of chemical reactions in which an electron-rich chemical species (known as a nucleophile) replaces a functional group within another electron-deficient molecule (known as the electrophile). The molecule that contains the electrophile and the leaving functional group is called the substrate.R. A. Rossi, R. H. de Rossi, Aromatic Substitution by the SRN1 Mechanism, ACS Monograph Series No. 178, American Chemical Society, 1983. .

Functional group

In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the rest of the molecule's composition. This enables systematic prediction of chemical reactions and behavior of chemical compounds and the design of chemical synthesis. The reactivity of a functional group can be modified by other functional groups nearby.

Related publications (2)

1- and 2-fluoroalkyl carboxylates

Chat with Graph Search

Substituent effect on the competition between hetero-Diels-Alder and cheletropic additions of sulfur dioxide to 1-substituted buta-1,3-dienes

A fluoroisoprenylation sequence employing 2-fluoroalkenal derived azomethines as key intermediates: a stereocontrolled synthesis of 2-fluorogeraniol and 2-fluorofarnesol